Enantioselective organocatalysis

被引：529

作者：

Gaunt, Matthew J. ^{[1
]}

Johansson, Carin C. C. ^{[1
]}

McNally, Andy ^{[1
]}

Vo, Ngoc T. ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

DRUG DISCOVERY TODAY | 2007年 / 12卷 / 1-2期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/j.drudis.2006.11.004

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

Enantioselective organocatalysis has emerged as a powerful synthetic paradigm that is complementary to metal-catalysed transformations and has accelerated the development of new methods to make diverse chiral molecules. The operational simplicity, ready availability of catalysts and low toxicity associated with organocatalysis makes it an attractive method to synthesise complex structures. Here, we discuss the impact of enamine, iminium, nucleophilic and Bronsted acid catalysts in organic synthesis, and highlight key strategic methods to assemble useful molecules with high enantiomeric purity.

引用

页码：8 / 27

页数：20

共 116 条

[31] ASYMMETRIC SYNTHESIS OF BICYCLIC INTERMEDIATES OF NATURAL PRODUCT CHEMISTRY [J].

HAJOS, ZG ;

PARRISH, DR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1615-1621

[32] Direct organocatalytic asymmetric α-chlorination of aldehydes [J].

Halland, N ;

Braunton, A ;

Bachmann, S ;

Marigo, M ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (15) :4790-4791

[33] Asymmetric organocatalysis of 4+3 cycloaddition reactions [J].

Harmata, M ;

Ghosh, SK ;

Hong, XC ;

Wacharasindhu, S ;

Kirchhoefer, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (08) :2058-2059

[34] Cysteine-derived organocatalyst in a highly enantioselective intramolecular Michael reaction [J].

Hayashi, Y ;

Gotoh, H ;

Tamura, T ;

Yamaguchi, H ;

Masui, R ;

Shoji, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16028-16029

[35] Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].

Hayashi, Y ;

Gotoh, H ;

Hayashi, T ;

Shoji, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215

[36] Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst [J].

Herrera, RP ;

Sgarzani, V ;

Bernardi, L ;

Ricci, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) :6576-6579

[37] Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions [J].

Hoang, L ;

Bahmanyar, S ;

Houk, KN ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :16-17

[38] A powerful bronsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines [J].

Hoffmann, S ;

Seayad, AM ;

List, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7424-7427

[39]

HONGMING L, 2004, ANGEW CHEM INT EDIT, V44, P105

[40] Enantioselective organo-cascade catalysis [J].

Huang, Y ;

Walji, AM ;

Larsen, CH ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (43) :15051-15053

← 1 2 3 4 5 6 7 8 9 10 →