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Journal articles on the topic 'Chiral epoxides; Alkenes; Organic synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Gyuranová, Dominika, Radka Štadániová, Zuzana Hegyi, Róbert Fischer, and Martin Rebroš. "Production of Enantiopure Chiral Epoxides with E. coli Expressing Styrene Monooxygenase." Molecules 26, no. 6 (2021): 1514. http://dx.doi.org/10.3390/molecules26061514.

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Styrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic synthesis in the pharmaceutical industry, and many of them are produced on an industrial scale. Two-component recombinant styrene monooxygenase (SMO) from Marinobacterium litorale was expressed as a fused protein (StyAL2StyB) in Escherichia coli BL21(DE3). By high cell density fermentation, 35 gDCW/L o

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2

MaGee, David I., Peter J. Silk, Junping Wu, Peter D. Mayo, and Krista Ryall. "Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomus subsignaria (Hübner) (Lepidoptera: Geometridae)." Tetrahedron 67, no. 29 (2011): 5329–38. http://dx.doi.org/10.1016/j.tet.2011.05.015.

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3

Song, Feijie, Teng Zhang, Cheng Wang, and Wenbin Lin. "Chiral porous metal-organic frameworks with dual active sites for sequential asymmetric catalysis." Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences 468, no. 2143 (2012): 2035–52. http://dx.doi.org/10.1098/rspa.2012.0100.

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Metal-organic frameworks (MOFs) are a class of organic–inorganic hybrid materials built from metal-connecting nodes and organic-bridging ligands. They have received much attention in recent years owing to the ability to tune their properties for potential applications in various areas. Properly designed MOFs with uniform, periodically aligned active sites have shown great promise in catalysing shape-, size-, chemo-, regio- and stereo-selective organic transformations. This study reports the synthesis and characterization of two chiral MOFs (CMOFs 1 and 2 ) that are constructed from Mn-salen-de

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4

Besse, Pascale, and Henri Veschambre. "Chemical and biological synthesis of chiral epoxides." Tetrahedron 50, no. 30 (1994): 8885–927. http://dx.doi.org/10.1016/s0040-4020(01)85362-x.

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5

Lu, Xiao-Yu, Run-Chuang Jiang, Jia-Mei Li, Chuang-Chuang Liu, Qing-Qing Wang, and Hai-Pin Zhou. "Synthesis of gem-difluoroalkenes via nickel-catalyzed allylic defluorinative reductive cross-coupling of trifluoromethyl alkenes with epoxides." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3674–78. http://dx.doi.org/10.1039/d0ob00535e.

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6

Chan, T. H., L. M. Chen, D. Wang, and L. H. Li. "Enantioselective synthesis of epoxides via Sharpless epoxidation of alkenylsilanols." Canadian Journal of Chemistry 71, no. 1 (1993): 60–67. http://dx.doi.org/10.1139/v93-009.

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Enantioselective synthesis of simple epoxides can be achieved by Sharpless epoxidation of alkenylsilanols followed by protodesilylation of the chiral epoxysilanols. The approach has been applied to the synthesis of frontalin.

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7

Macías-Villamizar, Víctor E., Luís Cuca-Suárez, Santiago Rodríguez, and Florenci V. González. "Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans." Molecules 25, no. 3 (2020): 692. http://dx.doi.org/10.3390/molecules25030692.

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We report on the regio- and stereoselective synthesis of tetrahydrofurans by reaction between epoxides and alkenes in the presence of a Lewis acid. This is an unprecedented formal [3+2] cycloaddition reaction between an epoxide and an alkene. The chemical reaction represents a very concise synthesis of tetrahydrofurans from accessible starting compounds.

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8

Bojaryn, Kevin, Stefan Fritsch, and Christoph Hirschhäuser. "Iterative Synthesis of Alkenes by Insertion of Lithiated Epoxides into Boronic Esters." Organic Letters 21, no. 7 (2019): 2218–22. http://dx.doi.org/10.1021/acs.orglett.9b00517.

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9

Llopis, Natalia, and Alejandro Baeza. "HFIP-Promoted Synthesis of Substituted Tetrahydrofurans by Reaction of Epoxides with Electron-Rich Alkenes." Molecules 25, no. 15 (2020): 3464. http://dx.doi.org/10.3390/molecules25153464.

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In the present work, the employment of fluorinated alcohols, specifically 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), as solvent and promoter of the catalyst-free synthesis of substituted tetrahydrofuranes through the addition of electron-rich alkenes to epoxydes is described. The unique properties of this fluorinated alcohol, which is very different from their non-fluorinated analogs, allows carrying out this new straightforward protocol under smooth reaction conditions affording the corresponding adducts in moderate yields in the majority of cases. Remarkably, this methodology has allowed the

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10

Bednářová, Eva, Štefan Malatinec, and Martin Kotora. "Applications of Bolm’s Ligand in Enantioselective Synthesis." Molecules 25, no. 4 (2020): 958. http://dx.doi.org/10.3390/molecules25040958.

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One pathway for the preparation of enantiomerically pure compounds from prochiral substrates is the use of metal complex catalysis with chiral ligands. Compared to the other frequently used chiral ligands, chiral 2,2’-bipyridines have been underexploited, despite the data indicating that such ligands have considerable potential in synthetic chemistry. One of those is the so-called Bolm’s ligand, a compound possessing chiral alcohol moieties in the side chains attached to the 2,2’-bipyridine scaffold. Various metal salts have been used in combination with Bolm’s ligand as potent catalysts able

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11

Gui, Yuan, Jian Li, Chang-Shan Guo, Xin-Liang Li, Zhi-Feng Lu, and Zhi-Zhen Huang. "A New Chiral Organosulfur Catalyst for Highly Stereoselective Synthesis of Epoxides." Advanced Synthesis & Catalysis 350, no. 16 (2008): 2483–87. http://dx.doi.org/10.1002/adsc.200800453.

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12

Li, Zhi, and Wen-Bin Xie. "Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation." Synthesis 52, no. 15 (2020): 2127–46. http://dx.doi.org/10.1055/s-0039-1690874.

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Many chiral ethers have important physiological activities. Although many asymmetric hydroalkoxylations of olefins with alcohols or phenols have been developed to make chiral ethers, challenges still remain in achieving high reactivity and selectivity over an ever-increasing diversity of alkenes and alcohols. In this review, recent developments on catalytic asymmetric alkene hydroalkoxylations are summarized based on the substitution patterns of alkenes.1 Introduction2 Asymmetric Hydroalkoxylation of Non-Activated Alkenes2.1 Intramolecular Additions2.2 Intermolecular Additions3 Asymmetric Hydr

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13

Millar, Jocelyn G., and Edward W. Underhill. "Synthesis of chiral bis-homoallylic epoxides. A new class of lepidopteran sex attractants." Journal of Organic Chemistry 51, no. 24 (1986): 4726–28. http://dx.doi.org/10.1021/jo00374a046.

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14

Kawasaki, Tsuneomi, Masako Shimizu, Kenta Suzuki, Itaru Sato, and Kenso Soai. "Enantioselective synthesis induced by chiral epoxides in conjunction with asymmetric autocatalysis." Tetrahedron: Asymmetry 15, no. 23 (2004): 3699–701. http://dx.doi.org/10.1016/j.tetasy.2004.09.036.

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15

Chang, Tao, Lili Jin, and Huanwang Jing. "Bifunctional Chiral Catalyst for the Synthesis of Chiral Cyclic Carbonates from Carbon Dioxide and Epoxides." ChemCatChem 1, no. 3 (2009): 379–83. http://dx.doi.org/10.1002/cctc.200900135.

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16

Huang, Zhi-Zhen, and Wen-Hua Ou. "A Novel and Highly Efficient Asymmetric Synthesis of Epoxides via Chiral Telluronium Ylides." Synthesis 2005, no. 17 (2005): 2857–60. http://dx.doi.org/10.1055/s-2005-872169.

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17

Skotnitzki, Juri, Alexander Kremsmair, Bilal Kicin, Rakan Saeb, Vincent Ruf, and Paul Knochel. "Stereoselective anti-SN2′-Substitutions of Secondary Alkylcopper-Zinc Reagents with Allylic Epoxides: Total Synthesis of (3S,6R,7S)-Zingiberenol." Synthesis 52, no. 06 (2019): 873–81. http://dx.doi.org/10.1055/s-0039-1690766.

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Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti-SN2′-substitution and retention of configuration of the chiral alkylorganometallic, leading to chiral allylic alcohols. This method was used in a total synthesis of the natural product (3S,6R,7S)-zingiberenol in 8 steps and 9.7% overall yield [dr (3S,6R) = 99:1; dr (6R,7S) = 81:19] starting from commercially available 3-methyl-2-cyclohexenone.

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18

Qin, Shuanglin, Linbin Yao, Yunhao Luo, et al. "Synthesis of aziridines with multiple chiral substitutions by copper-catalyzed diastereoselective radical aminotrifluoromethylation of alkenes." Organic Chemistry Frontiers 7, no. 20 (2020): 3132–36. http://dx.doi.org/10.1039/d0qo00603c.

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A one-step catalytic and diastereoselective method for the synthesis of aziridines possessing multiple chiral substitutions by radical aminotrifluoromethylation of alkenes has been developed for the first time.

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19

da Silva Gomes, Roberto, Karla Mahender Reddy, and E. J. Corey. "Synthesis of Chiral Cyclic Alcohols from Chiral Epoxides by H or N Substitution with Frontside Displacement." Organic Letters 20, no. 19 (2018): 6310–13. http://dx.doi.org/10.1021/acs.orglett.8b02822.

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20

Liu, Bing, Wenbo Li, Hai-Hong Wu, and Junliang Zhang. "Enantiodivergent synthesis of 1,2-bis(diphenylphosphino)ethanes via asymmetric [3 + 2]-cycloaddition." Organic Chemistry Frontiers 6, no. 5 (2019): 694–98. http://dx.doi.org/10.1039/c8qo01404c.

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The present work provides efficient access to chiral 1,2-bis(diphenylphosphino)ethanes (DPPEs) directly from diphosphine oxide alkenes and azomethine ylides via asymmetric [3 + 2] cycloaddition. Both enantiomers of the products can be obtained in good to excellent diastereo- and enantioselectivities (up to >20 : 1 dr and 99% ee).

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21

Kotani, Shunsuke, Haruka Furusho, Masaharu Sugiura, and Makoto Nakajima. "Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides." Tetrahedron 69, no. 14 (2013): 3075–81. http://dx.doi.org/10.1016/j.tet.2013.01.066.

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22

Negishi, Ei-ichi. "Some newer aspects of organozirconium chemistry of relevance to organic synthesis. Zr-Catalyzed enantioselective carbometallation." Pure and Applied Chemistry 73, no. 2 (2001): 239–42. http://dx.doi.org/10.1351/pac200173020239.

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The reaction of terminal alkenes with trialkylalanes in the presence of chiral (NMI) 2ZrCl2 has been shown to be 70-75% ee for methylalumination and 90-95% ee for ethyl- and higher alkylalumination. It must involve an acyclic bimetallic process. Its scope, limitations, and applications to some natural products syntheses are discussed.

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23

Yuan, Xiao, Lili Lin, Weiliang Chen, Wangbin Wu, Xiaohua Liu, and Xiaoming Feng. "Synthesis of Chiral Tetrahydrofurans via Catalytic Asymmetric [3 + 2] Cycloaddition of Heterosubstituted Alkenes with Oxiranes." Journal of Organic Chemistry 81, no. 3 (2016): 1237–43. http://dx.doi.org/10.1021/acs.joc.5b02524.

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24

Lemmerer, Abraham, Brutiu, Roller, and Widhalm. "Synthesis, Structure, and Reactivity of Binaphthyl Supported Dihydro[1,6]diazecines." Molecules 24, no. 17 (2019): 3098. http://dx.doi.org/10.3390/molecules24173098.

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A short approach to chiral diaza-olefines from protected 2,2′-diamino-1,1′-binaphthyl is presented. Cis- and trans-olefines can be selectively obtained by twofold N-allylation followed by RCM or by bridging a 2,2′-diamino-1,1′-binaphthyl precursor with trans-1,4-dibromo-2-butene. Deprotection afforded cis- and trans-dihydro[1,6]diazecines 1 in 58 and 64% overall yield. The reactivity of the but-2-ene-1,4-diyl fragment was investigated yielding corresponding epoxides, diols, and mono- and dibromo products. In several cases rearrangements and participation of the proximate N-Boc group was observ

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25

Evans, Ben E., Kenneth E. Rittle, Carl F. Homnick, James P. Springer, Jordan Hirshfield, and Daniel F. Veber. "A stereocontrolled synthesis of hydroxyethylene dipeptide isosteres using novel, chiral aminoalkyl epoxides and .gamma.-(aminoalkyl)-.gamma.-lactones." Journal of Organic Chemistry 50, no. 23 (1985): 4615–25. http://dx.doi.org/10.1021/jo00223a037.

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26

Hayakawa, Ryuuichirou, and Makoto Shimizu. "Synthesis of Chiral Epoxides from Aldehydes Using Sulfur Ylide Derived from Reduced Product of Bakers' Yeast Reduction." Synlett 1999, no. 8 (1999): 1328–30. http://dx.doi.org/10.1055/s-1999-2830.

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27

Kelly, Richard. "Expression of concern: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5853. http://dx.doi.org/10.1039/c7ob90107k.

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Expression of concern for ‘Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II’ by Pradeep Kumar et al., Org. Biomol. Chem., 2012, 10, 6987–6994.

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28

Shan, Huanyu, Rihuang Pan, and Xufeng Lin. "Synthesis and application of a new chiral monodentate spiro phosphoramidite ligand based on hexamethyl-1,1′-spirobiindane backbone in asymmetric hydroamination/arylation of alkenes." Organic & Biomolecular Chemistry 16, no. 34 (2018): 6183–86. http://dx.doi.org/10.1039/c8ob01785a.

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29

Kumar, Pradeep, Abhishek Dubey, and Anand Harbindu. "Correction and removal of expression of concern: Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II." Organic & Biomolecular Chemistry 18, no. 27 (2020): 5264. http://dx.doi.org/10.1039/d0ob90090g.

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Correction and removal of expression of concern for ‘Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and l-(−)-CCG-II’ by Pradeep Kumar et al., Org. Biomol. Chem., 2012, 10, 6987–6994, DOI: 10.1039/C2OB25622C.

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30

Le, Tam Minh, Tamás Szilasi, Bettina Volford, András Szekeres, Ferenc Fülöp, and Zsolt Szakonyi. "Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands." International Journal of Molecular Sciences 20, no. 16 (2019): 4050. http://dx.doi.org/10.3390/ijms20164050.

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A library of isopulegol-based bi-, tri- and tetrafunctional chiral ligands has been developed from commercially available (−)-isopulegol and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. Michael addition of primary amines towards α-methylene-γ-butyrolactone, followed by reduction, was accomplished to provide aminodiols in highly stereoselective transformations. Stereoselective epoxidation of (+)-neoisopulegol, derived from natural (−)-isopulegol, and subsequent oxirane ring opening with primary amines afforded aminodiols. The regioselective ring closure of N-subst

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31

Motherwell, William B., Guillaume Bégis, Tom D. Sheppard, David E. Cladingboel, and Derek A. Tocher. "Synthesis of Enantiopure Aminocyclopropanes by Diastereoselective Addition of a Chiral Amino Substituted Organozinc Carbenoid to Alkenes." Synthesis, no. 19 (2005): 3186–88. http://dx.doi.org/10.1055/s-2005-918469.

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32

de los Santos, Jesús M., Ana M. Ochoa de Retana, Edorta Martínez de Marigorta, Javier Vicario, and Francisco Palacios. "Catalytic Asymmetric Darzens and Aza-Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines." ChemCatChem 10, no. 22 (2018): 5092–114. http://dx.doi.org/10.1002/cctc.201801026.

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33

Rieger, Bernhard, Gerhard Jany, Manfred Steimann, and Riad Fawzi. "Synthesis of Ethylene Bridged Biscyclopentadiene Ligand Precursor Compounds and Some of their ansa-Zirconocene Derivatives via Chiral Epoxides: A Synthetic Strategy of High Variability." Zeitschrift für Naturforschung B 49, no. 4 (1994): 451–58. http://dx.doi.org/10.1515/znb-1994-0404.

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The chiral ligand precursor systems [1-Cp1-R1-2-R2-2-Cp2]ethane 5a-d bearing two different cyclopentadienyl fragments (Cp1, Cp2 = Cp, Ind, Flu) and a variable bridge substitution pattern (R1, R2=H, Ph, cyclopentyl, cyclohexyl) were prepared starting from the corresponding epoxides. The solid state structures of six organic intermediates are reported in order to prove the stereochemistry of the ligand forming reactions. Treatment of the dilithio salts of 5a-d with ZrCl4 in CH2Cl2 afforded chiral ansa-zirconocene dichlorides (6a-d).

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34

Tiecco, Marcello, Lorenzo Testaferri, Francesca Marini, et al. "Selenium-promoted synthesis of enantiomerically pure substituted morpholines starting from alkenes and chiral aminoalcohols." Tetrahedron: Asymmetry 14, no. 17 (2003): 2651–57. http://dx.doi.org/10.1016/s0957-4166(03)00498-1.

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35

Zhu, C., M. Yang, J. Sun, Y. Zhu, and Y. Pan. "The Synthesis of New C2-Symmetric Chiral 1,4-Diamino Motif and Application in Catalytic Asymmetric Alkynylation of meso-Epoxides." Synlett, no. 6 (2004): 1122. http://dx.doi.org/10.1055/s-2004-822911.

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36

Zhu, Chengjian, Minghua Yang, Jiangtao Sun, Yuhua Zhu, and Yi Pan. "The Synthesis of New C2-Symmetric Chiral 1,4-Diamino Motif and Application in Catalytic Asymmetric Alkynylation of meso-Epoxides." Synlett, no. 3 (2004): 465–68. http://dx.doi.org/10.1055/s-2004-815401.

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37

de Carvalho, Leandro Lara, Robert Alan Burrow та Vera Lúcia Patrocinio Pereira. "Diastereoselective synthesis of nitroso acetals from (S,E)-γ-aminated nitroalkenes via multicomponent [4 + 2]/[3 + 2] cycloadditions promoted by LiCl or LiClO4". Beilstein Journal of Organic Chemistry 9 (30 квітня 2013): 838–45. http://dx.doi.org/10.3762/bjoc.9.96.

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Chiral nonracemic aminated nitroso acetals were synthesized via diastereoselective multicomponent [4 + 2]/[3 + 2] cycloadditions employing new (S,E)-γ-nitrogenated nitroalkenes 5a–c as heterodienes, ethyl vinyl ether (EVE) as a dienophile, and selected electron-deficient alkenes as 1,3-dipolarophiles. The employment of different organic solutions of LiClO4 or LiCl as promoter systems provided the respective nitroso acetals with yields from 34–72% and good levels of diastereoselectivity. In addition, the nitroso acetal 9c was transformed to the pyrrolizidin-3-one derivative 14c, proving the use

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38

Bunlaksananusorn, Tanasri, and Paul Knochel. "t-BuOK-Mediated Hydrophosphination of Functionalized Alkenes: A Novel Synthesis of Chiral P,N- and P,P-Ligands." Journal of Organic Chemistry 69, no. 14 (2004): 4595–601. http://dx.doi.org/10.1021/jo030383u.

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39

Wrzeszcz, Zuzanna, and Renata Siedlecka. "Heteroaromatic N-Oxides in Asymmetric Catalysis: A Review." Molecules 25, no. 2 (2020): 330. http://dx.doi.org/10.3390/molecules25020330.

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An increasing interest in the synthesis and use of optically active pyridine N-oxides as chiral controllers for asymmetric reactions has been observed in the last few years. Chiral heteroaromatic N-oxides can work as powerful electron-pair donors, providing suitable electronic environments in the transition state formed within the reaction. The nucleophilicity of the oxygen atom in N-oxides, coupled with a high affinity of silicon to oxygen, represent ideal properties for the development of synthetic methodology based on nucleophilic activation of organosilicon reagents. The application of chi

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40

Bégis, Guillaume, David E. Cladingboel, Laure Jerome, William B. Motherwell, and Tom D. Sheppard. "Asymmetric Synthesis of Aminocyclopropanes andN-Cyclopropylamino Alcohols Through Direct Amidocyclopropanation of Alkenes Using Chiral Organozinc Carbenoids." European Journal of Organic Chemistry 2009, no. 10 (2009): 1532–48. http://dx.doi.org/10.1002/ejoc.200801033.

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41

Tao, Jingran, Li-Mei Jin, and X. Peter Zhang. "Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis." Beilstein Journal of Organic Chemistry 10 (June 4, 2014): 1282–89. http://dx.doi.org/10.3762/bjoc.10.129.

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The Co(II) complex of a new D 2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to 85% ee). In addition to mild reaction conditions and generation of N2 as the only byproduct, this new metalloradical catalytic system is highlighte

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42

Coutouli-Argyropoulou, Evdoxia, Christos Kyritsis, and Milosz Ruszkowski. "Diastereoselective cycloaddition of bromonitrile oxide to sugar derived chiral alkenes. A possible route for the synthesis of higher deoxysugars." Arkivoc 2009, no. 12 (2009): 181–92. http://dx.doi.org/10.3998/ark.5550190.0010.c16.

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43

Nicholas, Kenneth M., and Chandrasekhar Bandari. "Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides." Synthesis 53, no. 02 (2020): 267–78. http://dx.doi.org/10.1055/s-0040-1707269.

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AbstractThe prospective utilization of abundant, CO2-neutral, renewable feedstocks is driving the discovery and development of new reactions that refunctionalize oxygen-rich substrates such as alcohols and polyols through C–O bond activation. In this review, we highlight the development of transition-metal-promoted reactions of renewable alcohols and epoxides that result in carbon–carbon bond-formation. These include reductive self-coupling reactions and cross-coupling reactions of alcohols with alkenes and arene derivatives. Early approaches to reductive couplings employed stoichiometric amou

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44

Halterman, Ronald L., and Timothy M. Ramsey. "Asymmetric synthesis of a sterically rigid binaphthyl-bridged chiral metallocene: asymmetric catalytic epoxidation of unfunctionalized alkenes." Organometallics 12, no. 8 (1993): 2879–80. http://dx.doi.org/10.1021/om00032a003.

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45

Hirano, Koji, and Masahiro Miura. "Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents." Pure and Applied Chemistry 86, no. 3 (2014): 291–97. http://dx.doi.org/10.1515/pac-2014-5004.

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Abstract A copper-catalyzed regioselective, stereospecific, and enantioselective aminoboration reaction of alkenes with bis(pinacolato)diboron and O-acylated hydroxylamines has been developed to deliver the corresponding β-aminoalkylboranes, which can be important building blocks in organic synthesis. In addition, this methodology has been applied to a formal regioselective hydroamination of styrenes by replacement of the diboron reagent with polymethylhydrosiloxane (PMHS). The catalytic asymmetric hydroamination is also possible by using an appropriate chiral biphosphine ligand.

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46

Whiting, Andrew, and Jing-Biao Chen. "Recent Advances in Copper-Catalyzed Asymmetric Hydroboration of Electron-Deficient Alkenes: Methodologies and Mechanism." Synthesis 50, no. 19 (2018): 3843–61. http://dx.doi.org/10.1055/s-0037-1609583.

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The efficient synthesis of enantioenriched organoboron compounds has been recognized as an important topic in recent years. As an update review, this article aims to select key achievements in copper-catalyzed, electron-deficient alkene enantioselective hydroboration methodologies since the beginning of 2017. In addition, it covers relevant mechanistic investigations developed over the last six years, as well as total synthesis applications for preparing 1,3-diols as important medicinal intermediates.1 Introduction2 Methodologies for Copper-Catalyzed Hydroboration2.1 α,β-Unsaturated Ketones an

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Sarma, Kuladip, Nishi Bhati, Naleen Borthakur, and Amrit Goswami. "A novel method for the synthesis of chiral epoxides from styrene derivatives using chiral acids in presence of Pseudomonas lipase G6 [PSL G6] and hydrogen peroxide." Tetrahedron 63, no. 36 (2007): 8735–41. http://dx.doi.org/10.1016/j.tet.2007.06.046.

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Shustov, Gennady V., Melanie K. Chandler, and Saul Wolfe. "Stereoselective synthesis of multiply substituted [1,2]oxazinan-3-ones via ring-closing metathesis." Canadian Journal of Chemistry 83, no. 2 (2005): 93–103. http://dx.doi.org/10.1139/v04-174.

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The title compounds are α-amino acids whose nitrogen atoms are enclosed within 4,5-disubstituted, six-membered cyclic hydroxamates and they are of interest as potential β-lactam surrogates. The compounds have been synthesized in the present work by functionalization of the double bonds of N-substituted 6H-[1,2]oxazin-3-ones, which are obtained upon successive reaction of the triflates of S-α-hydroxy esters with O-allylhydroxylamine and acryloyl chloride, followed by cyclization of the resulting R-α-N-acryloyl-N-allyloxyamino esters in the presence of the ring-closing metathesis (RCM) catalyst

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Wosińska-Hrydczuk, Marzena, and Jacek Skarżewski. "New Nitrogen, Sulfur-, and Selenium-Donating Ligands Derived from Chiral Pyridine Amino Alcohols. Synthesis and Catalytic Activity in Asymmetric Allylic Alkylation." Molecules 26, no. 12 (2021): 3493. http://dx.doi.org/10.3390/molecules26123493.

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Although many chiral ligands for asymmetric catalysis have been developed, there is still a need for new structures allowing the modular approach. Recently, easy synthesis of chiral pyridine-containing β-amino alcohols has been elaborated by opening respective epoxides with enantiomeric 1-phenylethylamine. This paper reports the synthetic transformation of β-amino alcohols into the new complexing pyridine-containing seleno- and thioethers. The amino alcohols were effectively converted to cyclic sulfonamidates, which were reacted with thiolates or phenyl selenide nucleophile. The reaction was d

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Cruz, Alejandro, Itzia I. Padilla-Martínez, and Maria E. Bautista-Ramirez. "Ephedrines as Chiral Auxiliaries in Enantioselective Alkylation Reactions of Acyl Ephedrine Amides and Esters: A Review." Current Organic Synthesis 15, no. 1 (2018): 38–83. http://dx.doi.org/10.2174/1570179414666170830125915.

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Background: In modern chemistry, the asymmetric synthesis for the preparation of high purity chiral compounds to be used as pharmaceuticals or additives in foods have been of capital importance. Chiral auxiliary reagents are used to control the stereochemistry of the reaction in the generation of new chiral compounds, in this context, Ephedra compounds (ephedrines and pseudoephedrines) and some of their derivatives have been broadly used as chiral ligands in catalysis or chiral inductors in asymmetric synthesis. Objective: This review focuses on recent progress in the use of ephedra compounds

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