Desymmetrization of meso-N-Acylaziridines with Benzenethiols Promoted by α,α-Diaryl-L-prolinols

被引：23

作者：

Lattanzi, Alessandra ^{[1
]}

Della Sala, Giorgio ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim, I-84084 Fisciano, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 12期

关键词：

Desymmetrization; Aziridines; Organocatalysis; Amino alcohols; Asymmetric catalysis; ENANTIOSELECTIVE DESYMMETRIZATION; CATALYZED DESYMMETRIZATION; ASYMMETRIC AMINOLYSIS; CHIRAL 1,2-DIOLS; AZIRIDINES; EPOXIDES; COMPLEXES; ALPHA; BETA-ENONES; EPOXIDATION; ALCOHOLS;

D O I：

10.1002/ejoc.200900095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,alpha-Diaryl-L-prolinols were disclosed to promote the desymmetrization of meso-N-acylaziridines with benzenethiols to afford the products in good yields and moderate enantio-selectivities (up to 61% ee), which can be greatly improved to >90% ee after a single recrystallization. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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页码：1845 / 1848

页数：4

相关论文

共 45 条

[1] The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines [J].

Arai, Kenzo ;

Lucarini, Simone ;

Salter, Matthew M. ;

Ohta, Kentaro ;

Yamashita, Yasuhiro ;

Kobayashi, Shuj .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) :8103-8111

[2] Insight into the mechanism of the asymmetric ring-opening aminolysis of 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane catalyzed by titanium/BINOLate/water system:: Evidence for the Ti(BINOLate)2-bearing active catalyst entities and the role of water [J].

Bao, Hongli ;

Zhou, Jing ;

Wang, Zheng ;

Guo, Yinlong ;

You, Tianpa ;

Ding, Kuiling .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (31) :10116-10127

[3] Asymmetric aminolysis of aromatic epoxides:: A facile catalytic enantioselective synthesis of anti-β-amino alcohols [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Massaccesi, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2004, 6 (13) :2173-2176

[4] Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ORGANIC LETTERS, 2004, 6 (22) :3973-3975

[5]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

[6] Kinetic aspects of nonlinear effects in asymmetric catalysis [J].

Blackmond, DG .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :402-411

[7] Effect of ionic liquids on epoxide hydrolase-catalyzed synthesis of chiral 1,2-diols [J].

Chiappe, Cinzia ;

Leandri, Elsa ;

Hammock, Bruce D. ;

Morisseau, Christophe .

GREEN CHEMISTRY, 2007, 9 (02) :162-168

[8]

Dalko P.I., 2007, ENANTIOSELECTIVE ORG

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] Asymmetric organocatalysis: From infancy to adolescence [J].

Dondoni, Alessandro ;

Massi, Alessandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (25) :4638-4660

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