Enantioselective organocatalytic reductive amination

被引：636

作者：

Storer, RI ^{[1
]}

Carrera, DE ^{[1
]}

Ni, Y ^{[1
]}

MacMillan, DWC ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 01期

关键词：

D O I：

10.1021/ja057222n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective organocatalytic reductive amination reaction has been accomplished. The development of a new chiral phosphoric acid catalyst has provided a convenient strategy for the enantioselective construction of protected primary amines and provided a highly stereoselective method for the reductive amination of heterocyclic amines. A diverse spectrum of ketone and amine substrates can be accommodated in high yield and excellent enantioselectivity. This new protocol realizes a key benefit of reductive amination versus imine reduction, in that ketimines derived from alkyl-alkyl ketones are unstable to isolation, a fundamental limitation that is comprehensively bypassed using this direct organocatalytic reductive amination. Copyright © 2006 American Chemical Society.

引用

页码：84 / 86

页数：3

共 36 条

[1] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
Akiyama, T
Morita, H
Itoh, J
Fuchibe, K
[J]. ORGANIC LETTERS, 2005, 7 (13) : 2583 - 2585
[2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
Akiyama, T
Itoh, J
Yokota, K
Fuchibe, K
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
[3] Alberts B., 2002, Molecular Biology of The Cell, V4th
[4] Blaser HU, 1999, SYNLETT, P867
[5] Selective hydrogenation for fine chemicals: Recent trends and new developments
Blaser, HU
Malan, C
Pugin, B
Spindler, F
Steiner, H
Studer, M
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) : 103 - 151
[6] Chemo- and enantioselective hydrosilylation of carbonyl and imino groups. An emphasis on non-traditional catalyst systems
Carpentier, JF
Bette, V
[J]. CURRENT ORGANIC CHEMISTRY, 2002, 6 (10) : 913 - 936
[7] Highly enantioselective reductive amination of simple aryl ketones catalyzed by Ir-f-Binaphane in the presence of titanium(IV) isopropoxide and iodine
Chi, YX
Zhou, YG
Zhang, XM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) : 4120 - 4122
[8] Enantioselective synthesis of α-amino nitriles from N-benzhydryl imines and HCN with a chiral bicyclic guanidine as catalyst
Corey, EJ
Grogan, MJ
[J]. ORGANIC LETTERS, 1999, 1 (01) : 157 - 160
[9] Thiourea-catalyzed enantioselective cyanosilylation of ketones
Fuerst, DE
Jacobsen, EN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) : 8964 - 8965
[10] Hantzsch A., 1882, LIEBIGS ANN CHEM, V215, P1, DOI [10.1002/jlac.18822150102, DOI 10.1002/JLAC.18822150102]

← 1 2 3 4 →