Enantioselective radical addition/trapping reactions with α,β-disubstituted unsaturated imides.: Synthesis of anti-propionate aldols

被引:67
作者
Sibi, MP [1 ]
Petrovic, G [1 ]
Zimmerman, J [1 ]
机构
[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA
关键词
D O I
10.1021/ja043371e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This manuscript describes a highly diastereo- and enantioselective intermolecular radical addition/hydrogen atom transfer to α,β-disubstituted enoates. Additionally, we show that anti-propionate aldol-like products can be easily prepared from α-methyl-β-acyloxyenoates in good yields and high diastereo- and enantioselectivities. Copyright © 2005 American Chemical Society.
引用
收藏
页码:2390 / 2391
页数:2
相关论文
共 32 条
[1]   Boron-mediated aldol reaction of carboxylic esters [J].
Abiko, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (06) :387-395
[2]   Tandem enantioselective conjugate addition: Electrophile trapping reactions. application in the formation of syn or anti aldols [J].
Alexakis, A ;
Trevitt, GP ;
Bernardinelli, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4358-4359
[3]   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
[4]   Catalytic enantioselective synthesis of prostaglandin E1 methyl ester using a tandem 1,4-addition-aldol reaction to a cyclopenten-3,5-dione monoacetal [J].
Arnold, LA ;
Naasz, R ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (24) :5841-5842
[5]   VERSATILE CHIRAL REAGENT FOR THE HIGHLY ENANTIOSELECTIVE SYNTHESIS OF EITHER ANTI OR SYN ESTER ALDOLS [J].
COREY, EJ ;
KIM, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4976-4977
[6]  
Curran D P, 1995, STEREOCHEMISTRY RADI
[7]   1,2-ASYMMETRIC INDUCTION IN RADICAL REACTIONS - DEUTERATION AND ALLYLATION REACTIONS OF BETA-OXY-ALPHA-BROMO ESTERS [J].
CURRAN, DP ;
RAMAMOORTHY, PS .
TETRAHEDRON, 1993, 49 (22) :4841-4858
[8]   1,2-ASYMMETRIC INDUCTION IN RADICAL REACTIONS - DEUTERATION AND ALLYLATION REACTIONS OF BETA-OXY-O-IODOANILIDES [J].
CURRAN, DP ;
ABRAHAM, AC .
TETRAHEDRON, 1993, 49 (22) :4821-4840
[9]   Rotational features of carbon-nitrogen bonds in N-aryl maleimides.: Atroposelective reactions of o-tert-butylphenylmaleimides [J].
Curran, DP ;
Geib, S ;
DeMello, N .
TETRAHEDRON, 1999, 55 (18) :5681-5704
[10]   Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes [J].
Denmark, SE ;
Wynn, T ;
Beutner, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13405-13407