Highly enantioselective water-compatible organocatalyst for Michael reaction of ketones to nitroolefins

被引:149
作者
Vishnumaya [1 ]
Singh, Vinod K. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
D O I
10.1021/ol070082x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chiral diamine was found to catalyze enantioselective addition of ketones to nitroolefins in aqueous/saline/organic media. The products were obtained with excellent diastereoselectivities (synlanti = 99:1) and enantioselectivities up to 99%. The reaction could be facilitated using a mild acid.
引用
收藏
页码:1117 / 1119
页数:3
相关论文
共 36 条
[11]   A new class of chiral pyrrolidine-pyridine conjugate base catalysts for use in asymmetric Michael addition reactions [J].
Ishii, T ;
Fujioka, S ;
Sekiguchi, Y ;
Kotsuki, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9558-9559
[12]   Hydrophobic amplification of noncovalent organocatalysis [J].
Kleiner, Christian M. ;
Schreiner, Peter R. .
CHEMICAL COMMUNICATIONS, 2006, (41) :4315-4317
[13]   Michael additions of aldehydes and ketones to β-nitrostyrenes in an ionic liquid [J].
Kotrusz, P ;
Toma, S ;
Schmalz, HG ;
Adler, A .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1577-1583
[14]  
Li C.J., 1997, ORGANIC REACTION AQU
[15]   Organic reactions in aqueous media with a focus on carbon-carbon bond formations: A decade update [J].
Li, CJ .
CHEMICAL REVIEWS, 2005, 105 (08) :3095-3165
[16]   Stereocontrolled creation of adjacent quaternary and tertiary stereocenters by a catalytic conjugate addition [J].
Li, HM ;
Wang, Y ;
Tang, L ;
Wu, FH ;
Liu, XF ;
Guo, CY ;
Foxman, BM ;
Deng, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :105-108
[17]   Highly enantioselective conjugate addition of malonate and β-ketoester to nitroalkenes:: Asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloids [J].
Li, HM ;
Wang, Y ;
Tang, L ;
Deng, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9906-9907
[18]   Stereoselective organic reactions in water [J].
Lindström, UM .
CHEMICAL REVIEWS, 2002, 102 (08) :2751-2771
[19]   Efficient proline-catalyzed Michael additions of unmodified ketones to nitro olefins [J].
List, B ;
Pojarliev, P ;
Martin, HJ .
ORGANIC LETTERS, 2001, 3 (16) :2423-2425
[20]   Functionalized chiral ionic liquids as highly efficient asymmetric organocatalysts for Michael addition to nitroolefins [J].
Luo, Sanzhong ;
Mi, Xueling ;
Zhang, Long ;
Liu, Song ;
Xu, Hui ;
Cheng, Jin-Pei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3093-3097