2-Acetoxyacrylonitrile: use as electrophile equivalent to acetaldehyde in the asymmetric Michael reaction using chiral imines

被引:18
作者
Keller, L [1 ]
Camara, C [1 ]
Pinheiro, A [1 ]
Dumas, F [1 ]
d'Angelo, J [1 ]
机构
[1] Univ Paris Sud, Ctr Etud Pharmaceut, UA CNRS, F-92296 Chatenay Malabry, France
关键词
chiral imines; Michael reactions; 2-acetoxyacrylonitrile; stereocontrol;
D O I
10.1016/S0040-4039(00)01971-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric Michael addition reaction between a variety of chiral imines and 2-acetoxyacrylonitrile, an electrophile equivalent to acetaldehyde, was reported. The resulting adducts were obtained in fair yields and with de and ee greater than or equal to 95%. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:381 / 383
页数:3
相关论文
共 14 条
[1]   THE ASYMMETRIC MICHAEL REACTION USING CHIRAL IMINES UNDER NEUTRAL CONDITIONS - STEREOCHEMICAL EVIDENCES IN SUPPORT OF A CYCLIC TRANSITION-STATE [J].
AMBROISE, L ;
DESMAELE, D ;
MAHUTEAU, J ;
DANGELO, J .
TETRAHEDRON LETTERS, 1994, 35 (52) :9705-9708
[2]   THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].
BURGESS, EM ;
PENTON, HR ;
TAYLOR, EA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31
[3]   Efficient access to virtually enantiopure alpha-dialkyl-, alpha-acetoxy-, and alpha-acetamido esters [J].
Cave, C ;
LePorhielCastellon, Y ;
Daley, V ;
Riche, C ;
Chiaroni, A ;
dAngelo, J .
TETRAHEDRON LETTERS, 1997, 38 (50) :8703-8706
[4]   Stereochemical aspects in the asymmetric Michael addition of chiral imines to substituted electrophilic alkenes [J].
Cave, C ;
Desmaele, D ;
dAngelo, J ;
Riche, C ;
Chiaroni, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13) :4361-4368
[5]   The origin of the stereoselectivity in the asymmetric Michael reaction using chiral imines secondary enamines under neutral conditions: a computational investigation [J].
Dau, METH ;
Riche, C ;
Dumas, F ;
d'Angelo, J .
TETRAHEDRON-ASYMMETRY, 1998, 9 (06) :1059-1064
[6]   A simple, efficient access to functionalized pyrrolobenzazepines related to the ABC core of cephalotaxine [J].
deOliveira, ER ;
Dumas, F ;
dAngelo, J .
TETRAHEDRON LETTERS, 1997, 38 (21) :3723-3726
[7]   ENANTIOSELECTIVE SYNTHESIS OF OXA-SPIRO COMPOUNDS [J].
DESMAELE, D ;
DANGELO, J .
TETRAHEDRON LETTERS, 1989, 30 (03) :345-348
[8]  
Gassama A, 2000, EUR J ORG CHEM, V2000, P3165, DOI 10.1002/1099-0690(200009)2000:18<3165::AID-EJOC3165>3.0.CO
[9]  
2-7
[10]   MODEL STUDIES FOR THE SYNTHESIS OF QUASSINOIDS .1. CONSTRUCTION OF THE BCE RING-SYSTEM [J].
KRAUS, GA ;
TASCHNER, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1175-1176