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Journal articles on the topic 'Amine; Chiral auxiliary'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

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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2

Morandini, Anna, Arianna Rossetti, and Alessandro Sacchetti. "Lipase-Catalyzed Kinetic Resolution of Alcohols as Intermediates for the Synthesis of Heart Rate Reducing Agent Ivabradine." Catalysts 11, no. 1 (2021): 53. http://dx.doi.org/10.3390/catal11010053.

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Ivabradine (Corlanor®), is a chiral benzocycloalkane currently employed and commercialized for the treatment of chronic stable angina pectoris and for the reduction in sinus tachycardia. The eutomer (S)-ivabradine is usually produced via chiral resolution of intermediates, by employing enantiopure auxiliary molecules or through preparative chiral HPLC separations. Recently, more sustainable biocatalytic approaches have been reported in literature for the preparation of the chiral amine precursor. In this work, we report on a novel biocatalyzed pathway, via a resolution study of a key alcohol i

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3

Nugent, Thomas C., Richard Vaughan Williams, Andrei Dragan, Alejandro Alvarado Méndez, and Andrei V. Iosub. "An investigation of the observed, but counter-intuitive, stereoselectivity noted during chiral amine synthesis via N-chiral-ketimines." Beilstein Journal of Organic Chemistry 9 (October 15, 2013): 2103–12. http://dx.doi.org/10.3762/bjoc.9.247.

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The default explanation for good to high diastereomeric excess when reducing N-chiral imines possessing only mediocre cis/trans-imine ratios (>15% cis-imine) has invariably been in situ cis-to-trans isomerization before reduction; but until now no study unequivocally supported this conclusion. The present study co-examines an alternative hypothesis, namely that some classes of cis-imines may hold conformations that erode the inherent facial bias of the chiral auxiliary, providing more of the trans-imine reduction product than would otherwise be expected. The ensuing experimental and computa

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4

Talsi, Evgenii P., Anna A. Bryliakova, Roman V. Ottenbacher, Tatyana V. Rybalova, and Konstantin P. Bryliakov. "Chiral Autoamplification Meets Dynamic Chirality Control to Suggest Nonautocatalytic Chemical Model of Prebiotic Chirality Amplification." Research 2019 (November 4, 2019): 1–9. http://dx.doi.org/10.34133/2019/4756025.

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Oxidative kinetic resolution of 1-phenylethanol in the presence of manganese complexes, bearing conformationally nonrigid achiral bis-amine-bis-pyridine ligands, in the absence of any exogenous chiral additives, is reported. The only driving force for the chiral discrimination is the small initial enantiomeric imbalance of the scalemic (nonracemic) substrate: the latter dynamically controls the chirality of the catalyst, serving itself as the chiral auxiliary. In effect, the ee of 1-phenylethanol increases monotonously over the reaction course. This dynamic control of catalyst chirality by the

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5

Katagiri, Toshimasa, Naomi Iguchi, Tomomi Kawate, Satoshi Takahashi, and Kenji Uneyama. "Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons–Smith cyclopropanation of allylic amine." Tetrahedron: Asymmetry 17, no. 8 (2006): 1157–60. http://dx.doi.org/10.1016/j.tetasy.2006.04.031.

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6

Zimuwandeyi, Memory, Manuel A. Fernandes, Amanda L. Rousseau, and Moira L. Bode. "Total synthesis of ent-pavettamine." Beilstein Journal of Organic Chemistry 17 (June 10, 2021): 1440–46. http://dx.doi.org/10.3762/bjoc.17.99.

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Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C2 symmetry and a 1,3-syn-diol moiety on a C10 carbon backbone – one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the first total synthesis of the enantiomer of pavettamine, ent-pavettamine. The symmetrical structure of the molecule allows for the synthesis of a common C5 fragment that can be divergently transformed into two synthons for later conv

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7

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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8

Pichler, Mathias, Johanna Novacek, Raphaël Robiette, et al. "Asymmetric syntheses of three-membered heterocycles using chiral amide-based ammonium ylides." Organic & Biomolecular Chemistry 13, no. 7 (2015): 2092–99. http://dx.doi.org/10.1039/c4ob02318h.

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9

Han, Jianlin, Ryosuke Takeda, Xinyi Liu, et al. "Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid." Molecules 24, no. 24 (2019): 4521. http://dx.doi.org/10.3390/molecules24244521.

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Enantiomerically pure derivatives of 2-amino-4,4,4-trifluorobutanoic acid are in great demand as bioisostere of leucine moiety in the drug design. Here, we disclose a method specifically developed for large-scale (>150 g) preparation of the target (S)-N-Fmoc-2-amino-4,4,4-trifluorobutanoic acid. The method employs a recyclable chiral auxiliary to form the corresponding Ni(II) complex with glycine Schiff base, which is alkylated with CF3–CH2–I under basic conditions. The resultant alkylated Ni(II) complex is disassembled to reclaim the chiral auxiliary and 2-amino-4,4,4-trifluorobutanoic aci

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10

Brittain, William D. G., Brette M. Chapin, Wenlei Zhai, et al. "The Bull–James assembly as a chiral auxiliary and shift reagent in kinetic resolution of alkyne amines by the CuAAC reaction." Organic & Biomolecular Chemistry 14, no. 46 (2016): 10778–82. http://dx.doi.org/10.1039/c6ob01623e.

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The Bull–James boronic acid assembly is used simultaneously as a chiral auxiliary for kinetic resolution and as a chiral shift reagent for in situ enantiomeric excess (ee) determination by <sup>1</sup>H NMR spectroscopy.

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11

Mitra, Debarati, Arjun Sengupta, Kumar Biradha, and Amit Basak. "Asymmetric cyclopropanation using amino acid as chiral auxiliary." Tetrahedron: Asymmetry 19, no. 23 (2008): 2678–81. http://dx.doi.org/10.1016/j.tetasy.2008.11.009.

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12

Chen, Chou-Hsiung, Sivaneswary Genapathy, Peter M. Fischer, and Weng C. Chan. "A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues." Org. Biomol. Chem. 12, no. 48 (2014): 9764–68. http://dx.doi.org/10.1039/c4ob02107j.

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Utilising a chiral auxiliary-facilitated Strecker amino acid synthesis strategy, indole-substituted (S)-tryptophans have been obtained from corresponding indoles; the former in turn were used for the synthesis of a potent antibacterial agent, argyrin and its analogues.

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13

Manenti, Marco, Stefano Gazzotti, Leonardo Lo Presti, Giorgio Molteni та Alessandra Silvani. "Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives". Organic & Biomolecular Chemistry 19, № 33 (2021): 7211–16. http://dx.doi.org/10.1039/d1ob01303c.

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The Cu-catalysed addition of 1,1-diborylmethane to isatin ketimines, coupled with the application of Ellman's chiral auxiliary strategy, provides easy access to various boron-containing peptidomimetic derivatives and spirocyclic hemiboronic esters.

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14

WALDMANN, H. "ChemInform Abstract: Amino Acid Esters as Chiral Auxiliary Groups." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203292.

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15

Xiong, Yiwen, Haibo Mei, Lingmin Wu, Jianlin Han, Yi Pan та Guigen Li. "Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction". Beilstein Journal of Organic Chemistry 10 (13 березня 2014): 653–59. http://dx.doi.org/10.3762/bjoc.10.57.

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A variety of chiral N-phosphinyl α-imino esters have been synthesized for the first time from ketoesters and phosphinylamide, which were then reduced by L-selectride to give the corresponding N-phosphinyl-protected α-amino esters. The reduction proceeded very well with excellent chemical yields (88–98%) as well as high diastereoselectivities (96:4 to 99:1). Some of these products could be obtained without column chromatography and recrystallization. The chiral phosphinyl auxiliary could be easily cleaved under acidic conditions.

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16

Langer, Peter, Silvio Parpart, Zorayr Mardiyan, et al. "Synthesis of Optically Pure (S,E)-2-Amino-5-arylpent-4-enoic Acids by Heck Reactions of Nickel Complexes." Synlett 29, no. 06 (2018): 793–98. http://dx.doi.org/10.1055/s-0037-1609094.

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Starting from commercially available building blocks a variety of enantiomerically pure (S)-2-amino-4-enoic acids has been synthesized by the Heck reaction using Ni-(S)-BPB {Nickel-N-[(S)-benzylprolyl]aminobenzophenone} as a chiral auxiliary. The reactions proceeded in very good yields and with high E-selectivity.

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17

Jiang, Shende, Guang Yang, Shuanglin Qin та ін. "An Efficient Method for Constructing Cyclic β-Amino Acids Bearing Quaternary Stereocenters". Synlett 30, № 05 (2019): 593–99. http://dx.doi.org/10.1055/s-0037-1611718.

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This paper describes an efficient method for constructing cyclic β-amino acids bearing quaternary stereocenters. NaHMDS-promoted asymmetric α-alkylation was employed to obtain the key intermediates with quaternary stereogenic centers, which were subsequently reduced by NaBH4 in 10% methanol in THF, with high yields and high diastereoselectivities. By removing the allyl ester group and the chiral auxiliary, the corresponding cyclic β-amino acid hydrochlorides were finally obtained.

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18

Zhou, Wei, Qingwei Xiao, Yuanyuan Chang, et al. "Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents." Heterocyclic Communications 25, no. 1 (2019): 116–21. http://dx.doi.org/10.1515/hc-2019-0019.

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AbstractHerein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.

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19

Zadsirjan, Vahideh, and Majid M. Heravi. "Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review." Current Organic Synthesis 15, no. 1 (2018): 3–20. http://dx.doi.org/10.2174/1570179414666170601115831.

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Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated ca

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20

Mas-Roselló, Josep, Mary Okoh та Jonathan Clayden. "Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles". Chemical Communications 54, № 78 (2018): 10985–88. http://dx.doi.org/10.1039/c8cc06833j.

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21

Reissig, Hans-Ulrich, Arndt Hausherr, and Reinhold Zimmer. "Additions of Carbohydrate-Derived Alkoxyallenes to Imines and Subsequent Reactions to Enantiopure 2,5-Dihydropyrrole Derivatives." Synthesis 51, no. 02 (2018): 486–99. http://dx.doi.org/10.1055/s-0037-1609942.

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The additions of six alkoxyallenes bearing carbohydrate-derived chiral auxiliaries to imines were systematically studied. The reactions of three lithiated 1-alkoxypropa-1,2-dienes with an N-tosyl imine revealed that the diacetone fructose-derived auxiliary provided the highest diastereoselectivity of 91:9. The preferred absolute configuration of the newly formed stereogenic center was determined by subsequent ozonolysis of the allene moiety, transesterification and comparison with literature data. The analogous reactions of three axially chiral 3-nonyl-substituted 1-alkoxyallenes with these au

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22

Tovar-Gudiño, Erika, Rosmarbel Morales-Nava, and Mario Fernández-Zertuche. "Diasteroselective conjugate addition of diethylaluminum cyanide to a conjugated N-enoyl system: an alternative synthesis of (S)-pregabalin." Canadian Journal of Chemistry 92, no. 1 (2014): 45–48. http://dx.doi.org/10.1139/cjc-2013-0397.

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We have explored in this work the conjugate addition of diethylaluminum cyanide (Nagata’s reagent) to an N-enoyl system bearing the (R)-4-phenyl-2-oxazolidinone chiral auxiliary. Since this method provided a practical synthesis of γ-amino acids, we report the conjugate addition of diethylaluminum cyanide as the key step in the synthesis of (S)-pregabalin 1 in a five-step sequence of reactions from commercially available starting materials.

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23

Kim, Yong Hae, Chang Hong Ko, Doo Young Jung, and Min Kyun Kim. "Asymmetric Synthesis of 1,2-Amino Alcohols Usingtert-Butanesulfinimines as Chiral Auxiliary." Synlett, no. 2 (2005): 304–8. http://dx.doi.org/10.1055/s-2004-836070.

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24

WALDMANN, H. "ChemInform Abstract: Amino Acid Esters as Chiral Auxiliary Groups. Part 2." ChemInform 25, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199407314.

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25

Youn, So Won, Jun Young Choi, and Yong Hae Kim. "Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary." Chirality 12, no. 5-6 (2000): 404–7. http://dx.doi.org/10.1002/(sici)1520-636x(2000)12:5/6<404::aid-chir19>3.0.co;2-2.

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26

WALDMANN, H. "ChemInform Abstract: Amino Acid Esters as Chiral Auxiliary Groups. Part 1." ChemInform 24, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199331337.

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27

Nishiyama, Hisao, Jun-ichi Ito, Takushi Shiomi, Toru Hashimoto, Takeshi Miyakawa, and Megumi Kitase. "Chiral phenyl-bis(oxazoline) as an efficient auxiliary for asymmetric catalysis." Pure and Applied Chemistry 80, no. 4 (2008): 743–49. http://dx.doi.org/10.1351/pac200880040743.

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A new class of phenyl-bis(oxazoline) auxiliaries was readily prepared from isophthaloyl chloride and appropriate β-amino alcohols, and the derived rhodium complexes underwent new cyclization reactions at the metal center and exhibited high catalytic efficiency for asymmetric conjugate reduction of α,β-unsaturated carbonyl compounds and reductive aldol reactions of aldehydes and ketones.

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28

Pagire, Santosh K., Naoya Kumagai та Masakatsu Shibasaki. "Introduction of a 7-aza-6-MeO-indoline auxiliary in Lewis-acid/photoredox cooperative catalysis: highly enantioselective aminomethylation of α,β-unsaturated amides". Chemical Science 11, № 20 (2020): 5168–74. http://dx.doi.org/10.1039/d0sc01890b.

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An efficient cooperative chiral Lewis acid and photoredox catalytic system towards the highly enantioselective radical conjugate addition of α-amino radicals to α,β-unsaturated amides is developed with the implementation of unique auxiliaries.

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29

Castillo-Aguirre and Maldonado. "Preparation of Methacrylate-based Polymers Modified with Chiral Resorcinarenes and Their Evaluation as Sorbents in Norepinephrine Microextraction." Polymers 11, no. 9 (2019): 1428. http://dx.doi.org/10.3390/polym11091428.

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Aminomethylation reactions between chiral amino compounds (S)-(-)-1-phenylethylamine and l-proline with tetranonylresorcinarene and tetra-(4-hydroxyphenyl)resorcinarene in presence of formaldehyde were studied. The reaction between l-proline and resorcinarenes generated regioselectively chiral tetra-Mannich bases, due to the molecular incorporation of the fragment of the chiral amino acid. On the other hand, tetranonylresorcinarene and (S)-(-)-1-phenylethylamine formed regio- and diasteroselectively chiral tetrabenzoxazines, both by chiral auxiliary functionalization and by the transformation

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30

Popkov, Alexander, Ivana Císařová, Jana Sopková, Josef Jirman, Antonín Lyčka, and Konstantin A. Kochetkov. "Asymmetric Synthesis of (S)-2-Amino-3-(1-naphthyl)propanoic Acid via Chiral Nickel Complex. Crystal Structure, Circular Dichroism, 1H and 13C NMR Spectra of the Complex." Collection of Czechoslovak Chemical Communications 70, no. 9 (2005): 1397–410. http://dx.doi.org/10.1135/cccc20051397.

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The recently published environmentally friendly preparation of a glycine synthon 2 from regeneratable chiral auxiliary BPB ((S)-N-(2-benzoylphenyl)-N'-benzylprolinamide) was used for preparative asymmetric synthesis of the non-coded amino acid 3-(1-naphthyl)alanine (1). Full assignment of 1H and 13C NMR of both intermediate complex 3 and 1 and X-ray structure determination of complex 3 were made. Cotton effects observed in circular dichroism spectrum of complex 3 are consistent with published empirical rules.

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31

MATSUO, Jun-ichi, and Kenji KOGA. "Enantioselective .ALPHA.-Alkylation of Phenylacetic Acid Using a Chiral Bidentate Lithium Amide as a Chiral Auxiliary." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 12 (1997): 2122–24. http://dx.doi.org/10.1248/cpb.45.2122.

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32

Sturdivant, Jill, and Mitchell deLong. "Asymmetric Synthesis of Netarsudil: A New Therapeutic for Open-Angle Glaucoma." Synthesis 51, no. 04 (2018): 953–59. http://dx.doi.org/10.1055/s-0037-1610310.

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The asymmetric synthesis of a Rho kinase/norepinephrine transport inhibitor, netarsudil, the active component in the recently FDA-approved product Rhopressa™, is described herein. This concise six-step synthetic route utilizes the 2,4-dimethylbenzoate ester of a phenylacetic acid as the backbone of the β-amino acid’s framework. A chiral enolate of the Evans auxiliary, (R)-4-benzyloxazolidin-2-one, is used to direct the formation of the (S)-stereocenter by incorporating the N-Boc-protected β-amino methyl arm with high diastereoselectivity (96:4 dr) using N-Boc-1-aminomethylbenzotriazole as the

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33

Davies, Stephen G., Ai M. Fletcher, and James E. Thomson. "Direct asymmetric syntheses of chiral aldehydes and ketones via N-acyl chiral auxiliary derivatives including chiral Weinreb amide equivalents." Chemical Communications 49, no. 77 (2013): 8586. http://dx.doi.org/10.1039/c3cc45463k.

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34

Łyżwa, Piotr, and Marian Mikołajczyk. "Asymmetric synthesis of aminophosphonic acids mediated by chiral sulfinyl auxiliary: Recent advances." Pure and Applied Chemistry 82, no. 3 (2010): 577–82. http://dx.doi.org/10.1351/pac-con-09-11-06.

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New approaches to asymmetric synthesis of α-, β- and γ-aminophosphonic acids using enantiopure p-toluenesulfinimines as key reagents are reported. The utility of the devised methods is illustrated by the syntheses of enantiomeric aminophosphonic acids such as AP4, AP3, and its 3-amino isomer.

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35

Yamada, Tohru, Mitsuo Sato, Yasuhiko Gunji, and Taketo Ikeno. "Efficient Preparation of Optically PureC 2 -Symmetrical Cyclic Amines for Chiral Auxiliary." Synthesis 2004, no. 09 (2004): 1434–38. http://dx.doi.org/10.1055/s-2004-822366.

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36

Najdi, Samir, Daniel Reichlin, and Mark J. Kurth. "Enantioselective route to .gamma.-butyrolactones: chiral auxiliary mediated amide alkylation and iodolactonization." Journal of Organic Chemistry 55, no. 26 (1990): 6241–44. http://dx.doi.org/10.1021/jo00313a005.

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37

Westermann, Bernhard, Armin Walter, Ulrich Flörke, and Hans-Josef Altenbach. "Chiral Auxiliary Based Approach Toward the Synthesis of C-Glycosylated Amino Acids." Organic Letters 3, no. 9 (2001): 1375–78. http://dx.doi.org/10.1021/ol015743j.

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38

Bull, Steven D., Stephen G. Davies, Simon W. Epstein, Michael A. Leech та Jacqueline V. A. Ouzman. "A chiral relay auxiliary for the synthesis of homochiral α-amino acids". Journal of the Chemical Society, Perkin Transactions 1, № 15 (1998): 2321–30. http://dx.doi.org/10.1039/a803124j.

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39

Bull, Steven D., Stephen G. Davies, Simon W. Epstein та Jacqueline V. A. Ouzman. "Chiral relay auxiliary for the synthesis of enantiomerically pure α-amino acids". Chemical Communications, № 6 (1998): 659–60. http://dx.doi.org/10.1039/a800407b.

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40

Chernega, Alexander N., Stephen G. Davies, Christopher J. Goodwin, et al. "The Chiral AuxiliaryN-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxylamine: A Chiral Weinreb Amide Equivalent." Organic Letters 11, no. 15 (2009): 3254–57. http://dx.doi.org/10.1021/ol901174t.

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41

Boesten, Wilhelmus H. J., Jean-Paul G. Seerden, Ben de Lange та ін. "Asymmetric Strecker Synthesis of α-Amino Acids via a Crystallization-Induced Asymmetric Transformation Using (R)-Phenylglycine Amide as Chiral Auxiliary". Organic Letters 3, № 8 (2001): 1121–24. http://dx.doi.org/10.1021/ol007042c.

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42

Feringa, Ben L., Bert Strijtveen, and Richard M. Kellogg. "Enantiomeric excess determination without chiral auxiliary compounds. A new phosphorus-31 NMR method for amino acid esters and primary amines." Journal of Organic Chemistry 51, no. 26 (1986): 5484–86. http://dx.doi.org/10.1021/jo00376a100.

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43

Waldmann, Herbert, Gunther Schmidt, Henning Henke, and Michael Burkard. "Asymmetric Pictet–Spengler Reactions EmployingN,N-Phthaloyl Amino Acids as Chiral Auxiliary Groups." Angewandte Chemie International Edition in English 34, no. 21 (1995): 2402–3. http://dx.doi.org/10.1002/anie.199524021.

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44

Davies, Stephen G., and Darren J. Dixon. "N-Acyl “Quat” Pyrrolidinone Auxiliary as a Chiral Amide Equivalent via Direct Aminolysis." ChemInform 34, no. 1 (2003): no. http://dx.doi.org/10.1002/chin.200301032.

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45

Nagula, Gangadhar, Vincent J. Huber, Christopher Lum та Burton A. Goodman. "Synthesis of α-Substituted β-Amino Acids Using Pseudoephedrine as a Chiral Auxiliary". Organic Letters 2, № 22 (2000): 3527–29. http://dx.doi.org/10.1021/ol006614q.

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46

Davies, Stephen G., and Darren J. Dixon. "N-Acyl ‘Quat’ pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis." J. Chem. Soc., Perkin Trans. 1, no. 16 (2002): 1869–76. http://dx.doi.org/10.1039/b205326h.

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47

Davies, Stephen G., and Darren J. Dixon. "N-Acyl `Quat' Pyrrolidinone Auxiliary as a Chiral Amide Equivalent via Direct Aminolysis." Synlett 1998, no. 9 (1998): 963–64. http://dx.doi.org/10.1055/s-1998-1839.

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48

Chakraborty, T. K., K. Azhar Hussain та G. Venkat Reddy. "α-phenylglycinol as chiral auxiliary in diastereoselective strecker synthesis of α-amino acids". Tetrahedron 51, № 33 (1995): 9179–90. http://dx.doi.org/10.1016/0040-4020(95)00523-b.

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49

Kumagai, Naoya, and Masakatsu Shibasaki. "7-Azaindoline Auxiliary: A Versatile Attachment Facilitating Enantioselective C–C Bond-Forming Catalysis." Synthesis 51, no. 01 (2018): 185–93. http://dx.doi.org/10.1055/s-0037-1610412.

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Abstract:

This short review provides an overview of 7-azaindoline auxiliaries in asymmetric catalysis. 7-Azaindoline serves as a useful attachment to carboxylic acids, and the thus-formed 7-azaindoline amides are amenable to atom-economical C–C bond-forming reactions with high stereoselectivity. The attachment is used for the sake of gaining traction in promoting the reaction of interest and can be easily removed after enantioselective reactions. Both nucleophilic and electrophilic catalyses are realized with broad tolerance for functional groups, showcasing the usefulness of 7-azaindoline auxiliaries f

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50

Davies, Stephen G., Ai M. Fletcher, and James E. Thomson. "ChemInform Abstract: Direct Asymmetric Syntheses of Chiral Aldehydes and Ketones via N-Acyl Chiral Auxiliary Derivatives Including Chiral Weinreb Amide Equivalents." ChemInform 44, no. 46 (2013): no. http://dx.doi.org/10.1002/chin.201346227.

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