Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins

被引:192
作者
Betancort, JM
Sakthivel, K
Thayumanavan, R
Tanaka, F
Barbas, CF
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Biol Mol, La Jolla, CA 92037 USA
来源
SYNTHESIS-STUTTGART | 2004年 / 09期
关键词
asymmetric catalysis; Michael additions; organocatalysis; ketones; enamines;
D O I
10.1055/s-2004-822392
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Michael additions of a number of ketones and aldehydes to alkylidene malonates and nitro olefins were studied. The reactions employ small organic molecules as catalyst under mild reaction conditions and do not require preactivation of the carbonyl donors. These reactions afforded a variety of highly functionalized products in good yields with moderate to good enantioselectivity.
引用
收藏
页码:1509 / 1521
页数:13
相关论文
共 92 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].
Alexakis, A ;
Andrey, O .
ORGANIC LETTERS, 2002, 4 (21) :3611-3614
[3]   Organocatalytic Michael addition, a convenient tool in total synthesis. First asymmetric synthesis of (-)-botryodiplodin [J].
Andrey, O ;
Vidonne, A ;
Alexakis, A .
TETRAHEDRON LETTERS, 2003, 44 (43) :7901-7904
[4]   Asymmetric Michael addition of α-hydroxyketones to nitroolefins catalyzed by chiral diamine [J].
Andrey, O ;
Alexakis, A ;
Bernardinelli, G .
ORGANIC LETTERS, 2003, 5 (14) :2559-2561
[5]  
[Anonymous], 2000, CATALYTIC ASYMMETRIC
[6]   A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].
Arai, T ;
Sasai, H ;
Aoe, K ;
Okamura, K ;
Date, T ;
Shibasaki, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106
[8]  
Berner O. E., 2002, EUR J ORG CHEM, P1788
[9]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[10]   Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Barbas, CF .
TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444