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Journal articles on the topic 'Amine chirale'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Nodzewska, Aneta, Agnieszka Wadolowska, Katarzyna Podgorska, Damian Pawelski, and Ryszard Lazny. "Synthesis of Solid-phase Supported Chiral Amines and Investigation of Stereoselectivity of Aldol Reactions of Amine-free Tropinone Enolate." Current Organic Chemistry 23, no. 17 (2019): 1867–79. http://dx.doi.org/10.2174/1385272823666190916145332.

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Seven selected chiral mono-, di-, and tridentate amines supported on insoluble polymer were effectively prepared from corresponding primary amines or secondary amino alcohols and Merrifield resin. The reaction of the polymer-supported amines with excess n-butyllithium gave the corresponding lithium amide bases, which were tested in the aldol reactions of tropinone with benzaldehyde. The deprotonation reactions were carried out with or without separation of the lithium enolate from polymer-supported reagents. Using the procedure with separation of lithium enolate from supported chiral reagent d

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2

Liu, Lei, Dong-Hao Wang, Fei-Fei Chen, et al. "Development of an engineered thermostable amine dehydrogenase for the synthesis of structurally diverse chiral amines." Catalysis Science & Technology 10, no. 8 (2020): 2353–58. http://dx.doi.org/10.1039/d0cy00071j.

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3

Malcolmson, Steven J., Kangnan Li, and Xinxin Shao. "2-Azadienes as Enamine Umpolung Synthons for the Preparation of Chiral Amines." Synlett 30, no. 11 (2019): 1253–68. http://dx.doi.org/10.1055/s-0037-1611770.

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The development of new strategies for the preparation of chiral amines is an important objective in organic synthesis. In this Synpacts, we summarize our approach for catalytically accessing nucleophilic aminoalkyl metal species from 2-azadienes, and its application in generating a number of important but elusive chiral amine scaffolds. Reductive couplings with ketones and imines afford 1,2-amino tertiary alcohols and 1,2-diamines, respectively, whereas fluoroarylations of gem-difluoro-2-azadienes deliver α-trifluoromethylated benzylic amines.1 Introduction2 Background: Umpolung Strategies for

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4

Wünsch, Matthias, David Schröder, Tanja Fröhr, et al. "Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics." Beilstein Journal of Organic Chemistry 13 (November 15, 2017): 2428–41. http://dx.doi.org/10.3762/bjoc.13.240.

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The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at Cα, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24N-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman’s chiral sulfinamide provides chiralN-sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to

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5

Fraschetti, Caterina, Marco Pierini, Claudio Villani, Francesco Gasparrini, Antonello Filippi, and Maurizio Speranza. "Gas-phase structure and relative stability of proton-bound homo- and heterochiral clusters of tetra-amide macrocycles with amines." Collection of Czechoslovak Chemical Communications 74, no. 2 (2009): 275–97. http://dx.doi.org/10.1135/cccc2008155.

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The structure, stability, and CID pattern of proton-bound homochiral and heterochiral complexes, formed in the gas phase by the combination of two molecules of a chiral macrocyclic tetra-amide and an amine B, i.e. CH3NH2, (CH3)2NH, or (S)-(–)-1-phenylethylamine, have been examined by ESI-ITMS-CID mass spectrometry. With B = CH3NH2, the CID pattern is characterized by the predominant loss of B, accompanied by a much less extensive release of one tetra-amide molecule. With (S)-(–)-1-phenylethylamine, loss of a tetra-amide molecule efficiently competes with loss of B. Finally, with (CH3)2NH, loss

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6

Rychlewska, Urszula, Wioletta Bendzinska-Berus, Agnieszka Janiak, and Beata Warzajtis. "Mono- & ditrityl ethers, amines & amides – a family of multifaceted materials." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C670. http://dx.doi.org/10.1107/s2053273314093292.

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In the course of our recent study on the possible transfer of chirality from the stereogenic center(s) to the inherently helical triphenylmethyl (Tr) substituent we have structurally characterized mono- and ditrityl derivatives of chiral alcohols, amines and amides. During the course of our investigations we have experienced various kinds of packing peculiarities caused by the presence of sterically demanding chiral molecules, e.g. quasi-isomorphism between a pair of enantiomerically pure and racemic crystals, microporosity, lattice inclusion, multiplication of asymmetric units and pseudosymme

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7

Yu, Qiuhan, Weiwen Lu, Zhiqiang Ding, Min Wei, and Zhenya Dai. "Synthesis of novel chiral fluorescent sensors and their application in enantioselective discrimination of chiral carboxylic acids." Journal of Chemical Research 43, no. 9-10 (2019): 340–46. http://dx.doi.org/10.1177/1747519819867619.

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Novel chiral fluorescent sensors are synthesized from a dibromide containing a tetraphenylethylene moiety and enantiomerically pure amino alcohols and an amine. The sensors are applied for the chiral recognition of a wide range of chiral carboxylic acids and related derivatives.

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8

Burns, Christopher J., Leslie D. Field, Kikuko Hashimoto, Damon D. Ridley, Brian J. Petteys, and Michael Rose. "Synthesis of Stereoisomerically Pure Monoether Lipids." Australian Journal of Chemistry 52, no. 5 (1999): 387. http://dx.doi.org/10.1071/ch99001.

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Four stereoisomerically pure lipids have been synthesized which contain chirally pure phytanol (obtained through resolution of a chiral amide) and chiral glycerol moieties. The lipids were obtained in 7–13% overall yield in eight steps from commercially available materials.

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9

Li, Mao-Lin, Jin-Han Yu, Yi-Hao Li, Shou-Fei Zhu, and Qi-Lin Zhou. "Highly enantioselective carbene insertion into N–H bonds of aliphatic amines." Science 366, no. 6468 (2019): 990–94. http://dx.doi.org/10.1126/science.aaw9939.

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Aliphatic amines strongly coordinate, and therefore easily inhibit, the activity of transition-metal catalysts, posing a marked challenge to nitrogen-hydrogen (N–H) insertion reactions. Here, we report highly enantioselective carbene insertion into N–H bonds of aliphatic amines using two catalysts in tandem: an achiral copper complex and chiral amino-thiourea. Coordination by a homoscorpionate ligand protects the copper center that activates the carbene precursor. The chiral amino-thiourea catalyst then promotes enantioselective proton transfer to generate the stereocenter of the insertion pro

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10

Wang, Hongyue, Ge Qu, Jun-Kuan Li, et al. "Data mining of amine dehydrogenases for the synthesis of enantiopure amino alcohols." Catalysis Science & Technology 10, no. 17 (2020): 5945–52. http://dx.doi.org/10.1039/d0cy01373k.

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Five amine dehydrogenases (AmDHs) derived from amino acid dehydrogenases have been identified and evaluated for the stereoselective amination of α-/β-functionalized carbonyl compounds to synthesize chiral amino alcohols.

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11

Martens, Jürgen, Stefan Lübben та Walter Schwarting. "Stereoselective Reaction Mass Spectrometry with Cyclic α-Amino Acids". Zeitschrift für Naturforschung B 46, № 3 (1991): 320–25. http://dx.doi.org/10.1515/znb-1991-0312.

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Stereoselective reaction mass spectrometry in the chemical ionization (isobutane) mode has been used to detect the absolute configuration of enantiomerically pure cyclic α-amino acids. Thus, an enantiomerically pure cyclic α-amino acid was allowed to react on a micromole level with both enantiomers of a chiral selector and the mass spectra were detected. The relative abundances of characteristic ions formed by the diastereoselective reaction between the α-amino acid and the chiral selector of the same configuration were much higher than those ions formed by the α-amino acid and the chiral sele

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12

Yu, Jin-Sheng, Hidetoshi Noda, Naoya Kumagai та Masakatsu Shibasaki. "Direct Catalytic Asymmetric Mannich-Type Reaction of an α-CF3 Amide to Isatin Imines". Synlett 30, № 04 (2018): 488–92. http://dx.doi.org/10.1055/s-0037-1611642.

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An α-CF3 amide underwent direct asymmetric Mannich-type reaction to isatin imines in the presence of a chiral catalyst comprising a soft Lewis acid Cu(I), a chiral bisphosphine ligand, and Barton’s base. The Mannich adduct was converted in one step into a unique tricycle bearing a trifluoromethylated chiral center and an α-tertiary amine moiety.

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13

Wang, Wei, Xiaohan Xia, Guangling Bian, and Ling Song. "A chiral sensor for recognition of varied amines based on 19F NMR signals of newly designed rhodium complexes." Chemical Communications 55, no. 43 (2019): 6098–101. http://dx.doi.org/10.1039/c9cc01942a.

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A novel chiral octahedral rhodium complex containing fluorine has been developed to be an excellent chiral sensor for a variety of amines including diamines, monoamines, amino alcohols and amino acids, showing well distinguishable <sup>19</sup>F NMR signals and an accurate measurement of enantiomeric determination.

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14

Ross, Günther, та Ivar Ugi. "Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-D-xylopyranosylamine". Canadian Journal of Chemistry 79, № 12 (2001): 1934–39. http://dx.doi.org/10.1139/v01-186.

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Since 1961, the synthesis of α-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these α-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-β-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.Key words: stereoselective U-4CR, chiral amine component, amino carbohydrate, α-amino acid

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15

Kamiński, Z. J., K. J. Zajac, and K. Jastrzabek. "Synthesis and application of chiral triazine condensing reagents prepared from esters of amino acids." Acta Biochimica Polonica 48, no. 4 (2001): 1143–46. http://dx.doi.org/10.18388/abp.2001_3880.

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Treatment of cyanuric chloride with chiral amines or esters of chiral amino acids gave chiral 2,4-dichloro-6-alkylamino-1,3,5-triazines (2-5) in 49-69% yield, which were found useful as coupling reagents. Enantioselective activation and enantioselective aminolysis in the presence of 2-5 was observed.

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16

Rohde Jr, Laurence N., Matthias Zeller, and John A. Jackson. "Crystal structures of chiral 2-[bis(2-chloroethyl)amino]-1,3,2-oxazaphospholidin-2-one derivatives for the absolute configuration at phosphorus." Acta Crystallographica Section E Crystallographic Communications 74, no. 9 (2018): 1330–35. http://dx.doi.org/10.1107/s2056989018011349.

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`Nitrogen mustard' bis(2-chloroethyl)amine derivatives (2R,4S,5R)- and (2S,4S,5R)-2-[bis(2-chloroethyl)amino]-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one (2a and 2b, respectively), C14H21Cl2N2O2P, and (2R,4R)- and (2S,4R)-2-[bis(2-chloroethyl)amino]-4-isobutyl-1,3,2-oxazaphospholidin-2-one (3a and 3b, respectively), C10H21Cl2N2O2P, were synthesized as a mixture of diastereomers through a 1:1 reaction of enantiomerically pure chiral amino alcohols with bis(2-chloroethyl)phosphoramidic dichloride. Flash column chromatography yielded diastereomerically pure products, as supported by 31P N

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17

Wolińska, Ewa. "Chiral oxazoline ligands with two different six-membered azaheteroaromatic rings – synthesis and application in the Cu-catalyzed nitroaldol reaction." Heterocyclic Communications 22, no. 2 (2016): 85–94. http://dx.doi.org/10.1515/hc-2016-0001.

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AbstractSynthesis and catalytic activity of chiral ligands 5,6-diphenyl-3-{3-[(4S/R)-4-R/Ar-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl}amino-1,2,4-triazines 2 and their analogs 3 possessing an N-oxide function in the pyridine ring are described. The pivotal step in the synthesis of ligands 2 is the Buchwald-Hartwig Pd-catalyzed cross-coupling reaction between 3-bromo-5,6-diphenyl-1,2,4-triazine (7a) and enantiopure 3-(4,5-dihydro-1,3-oxazol-2-yl)pyridin-2-amines 6a–d. Aromatic nucleophilic substitution of chlorine in 3-chloro-5,6-diphenyl-1,2,4-triazine (7b) with 3-(4,5-dihydro-1,3-oxazol-2-yl)p

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18

Liu, Gongyi, Xianghe Zhang, Heng Wang, Hengjiang Cong, Xumu Zhang та Xiu-Qin Dong. "Synthesis of chiral α-substituted α-amino acid and amine derivatives through Ni-catalyzed asymmetric hydrogenation". Chemical Communications 56, № 36 (2020): 4934–37. http://dx.doi.org/10.1039/d0cc01220c.

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Efficient Ni-catalyzed asymmetric hydrogenation of cyclic N-sulfonyl ketimino esters and ketimines was successfully developed to prepare a series of chiral α-monosubstituted α-amino acid derivatives and amine derivatives with excellent results.

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19

Rodrigues, Carlos J. C., Manuel Ferrer та Carla C. C. R. de Carvalho. "ω-Transaminase-Mediated Asymmetric Synthesis of (S)-1-(4-Trifluoromethylphenyl)Ethylamine". Catalysts 11, № 3 (2021): 307. http://dx.doi.org/10.3390/catal11030307.

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The pivotal role played by ω-transaminases (ω-TAs) in the synthesis of chiral amines used as building blocks for drugs and pharmaceuticals is widely recognized. However, chiral bulky amines are challenging to produce. Herein, a ω-TA (TR8) from a marine bacterium was used to synthesize a fluorine chiral amine from a bulky ketone. An analysis of the reaction conditions for process development showed that isopropylamine concentrations above 75 mM had an inhibitory effect on the enzyme. Five different organic solvents were investigated as co-solvents for the ketone (the amine acceptor), among whic

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20

González-Martínez, Daniel, Nerea Fernández-Sáez, Carlos Cativiela, Joaquín Campos, and Vicente Gotor-Fernández. "Development of Biotransamination Reactions towards the 3,4-Dihydro-2H-1,5-benzoxathiepin-3-amine Enantiomers." Catalysts 8, no. 10 (2018): 470. http://dx.doi.org/10.3390/catal8100470.

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The stereoselective synthesis of chiral amines is an appealing task nowadays. In this context, biocatalysis plays a crucial role due to the straightforward conversion of prochiral and racemic ketones into enantiopure amines by means of a series of enzyme classes such as amine dehydrogenases, imine reductases, reductive aminases and amine transaminases. In particular, the stereoselective synthesis of 1,5-benzoxathiepin-3-amines have attracted particular attention since they possess remarkable biological profiles; however, their access through biocatalytic methods is unexplored. Amine transamina

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21

Majewski, Marek, Ryszard Lazny, and Agnieszka Ulaczyk. "Enantioselective ring opening of tropinone. A new entry into tropane alkaloids." Canadian Journal of Chemistry 75, no. 6 (1997): 754–61. http://dx.doi.org/10.1139/v97-091.

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The lithium enolate of tropinone reacts with alkyl chloroformates to give 6-N-carboalkoxy-N-methyl-2-cycloheptenones (4). These compounds can be produced enantioselectively, in up to 95% ee, if chiral lithium amides (derived from optically pure amines 5–7) are used for deprotonation of tropinone in the presence of additives. The effect of additives such as LiCl, LiBr, LiF, LiClO4, CeCl3, ZnCl2, LiOH, TMEDA, HMPA, and DMPU on enantioselectivity of this deprotonation–ring opening sequence varies from slight to very large depending on the chiral amide – additive combination. Especially large incr

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22

Hagemeister, Timo, Peter Jutzi, Anja Stammler, and Hans-Georg Stammler. "Chiral silicon-bridged 2-(N,N-dialkylamino)ethyl-substituted indenes as potential precursors for ansa-zirconocenes." Canadian Journal of Chemistry 81, no. 11 (2003): 1255–62. http://dx.doi.org/10.1139/v03-120.

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Chiral amino-functionalized silicon-bridged indene derivatives 4a4c were synthesized from 3-(2-(N,N-dialkylamino)ethyl)indenes 2a2c. The C-Si coupling reactions are regioselective, leading exclusively to the formation of 1,3-disubstituted isomers in a rac/meso ratio of 1:1, as indicated by NMR spectroscopy. The solid-state structure of the dimethylsilyl-bridged bisindene (R,R)-4a is described. The formation of corresponding ansa-zirconocenes via amine elimination chemistry was monitored by 1H NMR spectroscopy.Key words: amino-functionalized indenes, silicon-bridged, ansa-metallocenes, chiral

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23

De los Santos, Zeus A., Ransheng Ding, and Christian Wolf. "Quantitative chirality sensing of amines and amino alcohols via Schiff base formation with a stereodynamic UV/CD probe." Organic & Biomolecular Chemistry 14, no. 6 (2016): 1934–39. http://dx.doi.org/10.1039/c5ob02529j.

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24

Albert, Barbara, Martin Jansen, Jörg Jakobi та Eberhard Steckhan. "Synthesis and Crystal Structure of N-[(15,4R)-2-Oxo-pinanyl]-β-alanine Methylester". Zeitschrift für Naturforschung B 53, № 10 (1998): 1188–90. http://dx.doi.org/10.1515/znb-1998-1014.

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AbstractThe title compound, N-[(lS,4R)-2-oxo-pinanyl]-β-alanine methylester, is an important starting material for the electrochemical preparation of chiral amidoalkylation reagents in the synthesis of chiral β-substituted β-amino acid derivatives. The investigation of its crystal structure reveals an arrangement of the carbonyl group and the amine function, which is influenced by a hydrogen bonding interaction. This conformation makes the molecule especially appropriate for further synthetical modification

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25

Li, Na, Fan Yang, Hillary A. Stock, David V. Dearden, John D. Lamb, and Roger G. Harrison. "Resorcinarene-based cavitands with chiral amino acid substituents for chiral amine recognition." Organic & Biomolecular Chemistry 10, no. 36 (2012): 7392. http://dx.doi.org/10.1039/c2ob25613d.

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26

Wosińska-Hrydczuk, Marzena, and Jacek Skarżewski. "2-Oxiranyl-pyridines: Synthesis and Regioselective Epoxide Ring Openings with Chiral Amines as a Route to Chiral Ligands." Heteroatom Chemistry 2019 (October 9, 2019): 1–12. http://dx.doi.org/10.1155/2019/2381208.

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New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes. The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary. The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for 7 days at 80°C, affording a good yield of the amino alcohols. Except for styrene oxide which gave both α- and β-amino alcohols, the reactions led regioselectively to the corresponding diastereomer

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27

Böhmer, Wesley, Lucien Koenekoop, Timothée Simon та Francesco G. Mutti. "Parallel Interconnected Kinetic Asymmetric Transformation (PIKAT) with an Immobilized ω-Transaminase in Neat Organic Solvent". Molecules 25, № 9 (2020): 2140. http://dx.doi.org/10.3390/molecules25092140.

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Comprising approximately 40% of the commercially available optically active drugs, α-chiral amines are pivotal for pharmaceutical manufacture. In this context, the enzymatic asymmetric amination of ketones represents a more sustainable alternative than traditional chemical procedures for chiral amine synthesis. Notable advantages are higher atom-economy and selectivity, shorter synthesis routes, milder reaction conditions and the elimination of toxic catalysts. A parallel interconnected kinetic asymmetric transformation (PIKAT) is a cascade in which one or two enzymes use the same cofactor to

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28

An, Zhe, Lifeng Chen, Yitao Jiang, and Jing He. "Heterogeneous Synergistic Catalysis for Promoting Aza-Michael–Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline." Catalysts 9, no. 9 (2019): 713. http://dx.doi.org/10.3390/catal9090713.

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Heterogeneous synergistic catalysis by SBA-15 immobilized chiral amines catalysts has promoted efficient aza-Michael–Henry tandem reaction for the synthesis of chiral 3-Nitro-1,2-Dihydroquinoline. Final products in the asymmetric aza-Michael–Henry cascade reactions between 2-aminobenzaldehyde and β-nitrostyrolene were afforded in a yield of 85% and an enantiomeric excess (ee) value of 98% on (S)-(–)-2-aminomethyl-1-ethylpyrrolidine immobilized SBA-15. SBA-15-AEP catalyst has been also extended to the asymmetric aza-Michael–Henry cascade reaction of substituted R1-2-aminobenzaldehyde and R2-sub

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29

Bai, Song, Shan Liu, Yunying Zhu, et al. "Solvent-Free Synthesis and Antiviral Activity of Chiral Dialkyl 2-(Substituted-((4-(Pyridin-3-Yl)Pyrimidin-2-Yl)Amino)Methyl) Malonate." Journal of Chemical Research 42, no. 8 (2018): 428–33. http://dx.doi.org/10.3184/174751918x15339142171145.

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An efficient asymmetric synthesis of chiral β-amino acid ester derivatives containing a 4-(pyridin-3-yl)pyrimidin-2-yl amine moiety was developed. This catalytic asymmetric Mannich reaction gave target products in high yields (95%) and excellent enantioselectivities (>99% ee) using a cinchona-based squaramide catalyst under solvent-free, one-pot conditions. Antiviral bioassays indicated that some of the chiral products exhibited higher antiviral activities against tobacco mosaic virus than the commercial compound ribavirin.

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30

Potvin, Pierre G., and Benjamin G. Fieldhouse. "An NMR study of mixed, tartrate-containing TiIV complexes." Canadian Journal of Chemistry 73, no. 3 (1995): 401–13. http://dx.doi.org/10.1139/v95-053.

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The reactions of amines and amino alcohols with diisopropyl or diethyl R,R- or S,S-tartrate and Ti(OiPr)4 were examined by 1H and 13C NMR to obtain and characterize nonfluxional complexes with the tartrate units in novel binding modes. The mildly acidic 8-hydroxyquinoline and N-phenyl-N-benzoylhydroxylamine selectively formed the products of a double OiPr substitution, Ti2(tartrate)2(ligand)2(OiPr)2, and the products of double tartrate substitution, Ti(ligand)2(OiPr)2, while 2,4-pentanedione formed only the latter Basic amino alkanols formed diastereomerically pure Ti2(tartrate)2(aminoalkoxide

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31

Travagliante, Gabriele, Massimiliano Gaeta, Roberto Purrello, and Alessandro D’Urso. "Recognition and Sensing of Chiral Organic Molecules by Chiral Porphyrinoids: A Review." Chemosensors 9, no. 8 (2021): 204. http://dx.doi.org/10.3390/chemosensors9080204.

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Porphyrinoids are extremely attractive for their electronic, optical, and coordination properties as well as for their versatile substitution at meso/β-positions. All these features allow porphyrinoids to behave as chiroptical hosts for chiral recognition by means of non-covalent interactions towards chiral guests. Over the years, chiral discrimination of chiral molecules such as amino acids, alcohols, amines, hydroxy-carboxylic acids, etc. has aroused the interest of the scientific community. Hence, this review aims to report on the progress to date by illustrating some relevant research rega

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32

Dawood, Ayad W. H., Rodrigo O. M. A. de Souza, and Uwe T. Bornscheuer. "Asymmetric Synthesis of Chiral Halogenated Amines using Amine Transaminases." ChemCatChem 10, no. 5 (2018): 951–55. http://dx.doi.org/10.1002/cctc.201701962.

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33

Deng, Yongming, Qing-Qing Cheng, and Michael Doyle. "Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis." Synlett 28, no. 14 (2017): 1695–706. http://dx.doi.org/10.1055/s-0036-1588453.

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Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring hete

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34

Zhu, Yannan, and You Huang. "Organocatalyzed [3+3] Annulations for the Construction of Heterocycles." Synthesis 52, no. 08 (2020): 1181–202. http://dx.doi.org/10.1055/s-0039-1690810.

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Six-membered heterocyclic systems are widely distributed in many natural products and pharmaceuticals, and the construction of highly functionalized six-membered heterocyclic compounds is an important topic in modern organic synthesis. Organocatalyzed [3+3] annulations represents an important method for assembling a substantial variety of six-membered cycles that contain one or more heteroatoms. This review describes the development of organocatalyzed [3+3] annulations for the synthesis of six-membered heterocycles, including organocatalysis using secondary amines, tertiary amines, phosphines,

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35

Capobianco, Amedeo, Antonia Di Mola, Valentina Intintoli, et al. "Asymmetric tandem hemiaminal-heterocyclization-aza-Mannich reaction of 2-formylbenzonitriles and amines using chiral phase transfer catalysis: an experimental and theoretical study." RSC Advances 6, no. 38 (2016): 31861–70. http://dx.doi.org/10.1039/c6ra05488a.

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The first asymmetric synthesis of 3-amino-substituted isoindolinones was accomplished via cascade hemiaminal-heterocyclization-intramolecular aza-Mannich reaction of amines and 2-formylbenzonitriles using chiral phase transfer conditions (PTC).

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36

Villanueva-Kasis, Oscar, Denisse A. de Loera, Sandra L. Castañón-Alonso та ін. "Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines". Proceedings 9, № 1 (2018): 34. http://dx.doi.org/10.3390/ecsoc-22-05769.

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Four new α-β-unsaturated alkyl-ester chiral amines were synthesized in excellent yields (77–95%) via peptide couplings from their corresponding α-β-unsaturated alkyl-ester anilines and N-Boc protected chiral aminoacids. To our delight, these polyfunctionalized compounds are being used as starting reagents in Ugi-type three-component reactions (Ugi-3CR) together with alkyl- and aryl-aldehydes and a chain-ring tautomerizable amino acid-containing isocyanide to synthesize novel oxazole-based macrocycle precursors. Thus, the aim of this communication is to show our most recent results of the synth

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37

Pushina, Mariia, Sepideh Farshbaf, Elena G. Shcherbakova, and Pavel Anzenbacher. "A dual chromophore sensor for the detection of amines, diols, hydroxy acids, and amino alcohols." Chemical Communications 55, no. 31 (2019): 4495–98. http://dx.doi.org/10.1039/c9cc01051c.

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The determination of enantiomeric excess (ee) in various groups of chiral compounds, namely amines, amino alcohols, diols, and hydroxy acids is performed using a dual chromophore FRET/PET based sensor ensemble.

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38

Thomsen, Maren, Lilly Skalden, Gottfried J. Palm, Matthias Höhne, Uwe T. Bornscheuer, and Winfried Hinrichs. "Crystallographic characterization of the (R)-selective amine transaminase fromAspergillus fumigatus." Acta Crystallographica Section D Biological Crystallography 70, no. 4 (2014): 1086–93. http://dx.doi.org/10.1107/s1399004714001084.

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The importance of amine transaminases for producing optically pure chiral precursors for pharmaceuticals and chemicals has substantially increased in recent years. The X-ray crystal structure of the (R)-selective amine transaminase from the fungusAspergillus fumigatuswas solved by S-SAD phasing to 1.84 Å resolution. The refined structure at 1.27 Å resolution provides detailed knowledge about the molecular basis of substrate recognition and conversion to facilitate protein-engineering approaches. The protein forms a homodimer and belongs to fold class IV of the pyridoxal-5′-phosphate-dependent

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39

Tanaka, Koichi, Maya Kinoshita, Jun Kayahara, et al. "Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts." RSC Advances 8, no. 49 (2018): 28139–46. http://dx.doi.org/10.1039/c8ra05163a.

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Asymmetric ring-opening reactions of meso-epoxides by aromatic amines were achieved by using some chiral metal–organic frameworks. The corresponding β-amino alcohols were obtained with good yields and enantioselectivities (up to 97% ee).

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40

Gennari, Cesare, Chiara Monti, and Umberto Piarulli. "Rhodium-catalyzed asymmetric reactions with a dynamic library of chiral tropos phosphorus ligands." Pure and Applied Chemistry 78, no. 2 (2006): 303–10. http://dx.doi.org/10.1351/pac200678020303.

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Nineteen chiral tropos phosphorus ligands, based on a flexible (tropos) biphenol unit and a chiral P-bound alcohol (11 phosphites) or secondary amine (8 phosphoramidites), were screened, individually and as a combination of two, in various Rh-catalyzed asymmetric reactions. In the Rh-catalyzed asymmetric conjugate addition of phenylboronic acid to cyclic enones, enantiomeric excesses (ee's) up to 95 % were obtained with a 1:1 mixture of a phosphite [derived from (1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexanol] and a phosphoramidite [derived from (S,S)-2,5-diphenylpyrrolidine]. In the mixed Rh p

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41

Claeys-Bruno, Magalie, Jacques Pécaut, Michel Bardet, and Jean-Claude Marchon. "An improved chiroporphyrin shift reagent for the enantiomeric assay of amino acid derivatives by 1H NMR spectroscopy: evaluation of iodorhodium(III) tetramethylchiroporphyrin." Journal of Porphyrins and Phthalocyanines 06, no. 06 (2002): 396–402. http://dx.doi.org/10.1142/s108842460200049x.

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1 H NMR spectroscopic studies of amino ester complexation indicate that iodorhodium(III) tetramethylchiroporphyrin RhI(TMCP) has a single axial site available for the coordination of amine groups, and that it retains its iodo ligand trans to the coordinated amine. This conclusion is confirmed by the X-ray structure of the 1:1 adduct of n-propylamine with RhI(TMCP). This stoichiometry of amine binding makes RhI(TMCP) a superior chiral derivatizing agent relative to CoCl ( TMCP ), which gives 1:2 adducts. It may have a strong impact in the utilization of RhI(TMCP) for the enantiomeric assay of a

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42

Hili, Ryan, Sivaraj Baktharaman та Andrei K. Yudin. "Synthesis of Chiral Amines Using α-Amino Aldehydes". European Journal of Organic Chemistry 2008, № 31 (2008): 5201–13. http://dx.doi.org/10.1002/ejoc.200800604.

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43

Chen, Fei-Fei, Sebastian C. Cosgrove, William R. Birmingham, et al. "Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases." ACS Catalysis 9, no. 12 (2019): 11813–18. http://dx.doi.org/10.1021/acscatal.9b03889.

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Huang, Kejun, Xuehai Pei, Xiaogang Yin, and Zhiming Chen. "Novel Chiral Secondary Amine-Amide Catalysts Friedel-Craft Alkylation Reaction." Asian Journal of Chemistry 29, no. 3 (2017): 595–600. http://dx.doi.org/10.14233/ajchem.2017.20269.

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Abrahamson, Michael J., Eduardo Vázquez-Figueroa, Nicholas B. Woodall, Jeffrey C. Moore, and Andreas S. Bommarius. "Development of an Amine Dehydrogenase for Synthesis of Chiral Amines." Angewandte Chemie International Edition 51, no. 16 (2012): 3969–72. http://dx.doi.org/10.1002/anie.201107813.

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46

Ledingham, Edward T., and Ben W. Greatrex. "Aziridination and aza-Wharton Reactions of Levoglucosenone." Australian Journal of Chemistry 72, no. 5 (2019): 362. http://dx.doi.org/10.1071/ch18574.

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Efficient conditions have been developed for the diastereoselective aziridination of the biomass pyrolysis product (−)-levoglucosenone, via the reaction of primary aliphatic amines with 3-iodolevoglucosenone. In contrast to the reactions of aliphatic amines, the use of 4-methoxyaniline resulted in an aza-Michael-initiated dimerisation reaction, and 1,3-diphenylurea gave a 2-imidazolidinone. The aziridine products were transformed using the aza-Wharton reaction, affording novel sulfonamide and amine-substituted 6,8-dioxabicyclo[3.2.1]oct-3-enes with potential as sp3-rich chiral scaffolds.

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47

Gord Noshahri, Najme, Jamshid Fooladi, Christoph Syldatk та ін. "Screening and Comparative Characterization of Microorganisms from Iranian Soil Samples Showing ω-Transaminase Activity toward a Plethora of Substrates". Catalysts 9, № 10 (2019): 874. http://dx.doi.org/10.3390/catal9100874.

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In this study, soil microorganisms from Iran were screened for ω-transaminase (ω-TA) activity based on growth on minimal media containing (rac)-α-methylbenzylamine (rac-α-MBA) as a sole nitrogen source. Then, for the selection of strains with high enzyme activity, a colorimetric o-xylylendiamine assay was conducted. The most promising strains were identified by 16S rDNA sequencing. Five microorganisms showing high ω-TA activity were subjected to determine optimal conditions for ω-TA activity, including pH, temperature, co-solvent, and the specificity of the ω-TA toward different amine donors a

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48

Chebrouk, Farid, Khodir Madani, Brahim Cherfaoui, et al. "Hemi-Synthesis of Chiral Imine, Benzimidazole and Benzodiazepines from Essential Oil of Ammodaucus leucotrichus subsp. leucotrichus." Molecules 24, no. 5 (2019): 975. http://dx.doi.org/10.3390/molecules24050975.

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The hemi-synthesis of chiral imine, benzimidazole and benzodiazepine structures is reported by the condensation of (S)-(−)-perillaldehyde, the major phytochemical of Ammodaucus leucotrichus subsp. leucotrichus essential oil, with different amine derivatives of 2,3-diaminomaleonitrile, o-phenylenediamine and 3-[(2-aminoaryl)amino]dimedone. The reaction proceeds in situ at ambient temperature without prior isolation of the natural (S)-(−)-perillaldehyde. Final products precipitate in the ethanolic reaction medium. 2D NMR and single-crystal X-ray diffraction studies were used to unequivocally cha

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49

Luo, Sanzhong, Zongbin Jia, and Qi Yang. "Photoredox-Mediated Asymmetric Cross-Dehydrogenative Coupling of Enones and Tertiary Amines by Chiral Primary Amine Catalysis." Synthesis 53, no. 16 (2021): 2809–18. http://dx.doi.org/10.1055/a-1463-4219.

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AbstractA catalytic asymmetric dehydrogenative cross-coupling reaction between enones and tertiary amines enabled by synergistic photoredox and chiral primary amine catalysis is reported. The reaction was proposed to proceed via the interception of iminium ion intermediate, in situ generated from photoredox oxidation, by dienamine at α-position, followed by isomerization, leading to aza-Morita–Baylis–Hillman-type products with good diastereo- and enantioselectivity.

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Nelson, Eryn, Jeffrey S. S. K. Formen, and C. Wolf. "Rapid organocatalytic chirality analysis of amines, amino acids, alcohols, amino alcohols and diols with achiral iso(thio)cyanate probes." Chemical Science 12, no. 25 (2021): 8784–90. http://dx.doi.org/10.1039/d1sc02061g.

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Organocatalysis with a simple arylisocyanate probe enables accelerated optical concentration and enantiomeric ratio determination of a large variety of chiral compounds based on straightforward UV/CD analysis.

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