An enantioselective indium-mediated allylation reaction of aldehydes and ketones in dichloromethane

被引:60
作者
Loh, TP [1 ]
Zhou, JR [1 ]
Li, XR [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 119260, Singapore
关键词
enantioselectivity; indium; allylation; carbonyl; trifluoromethyl;
D O I
10.1016/S0040-4039(99)01976-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective indium-mediated addition reaction of allylic bromides to carbonyl compounds was achieved in dichloromethane in the presence of (-)-cinchonidine. The desired products were obtained in moderate to excellent yields and with up to 75% enantioselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9333 / 9336
页数:4
相关论文
共 17 条
[1]   SYNTHESIS OF ENANTIOMERICALLY ENRICHED HOMOALLYLIC ALCOHOLS AND OF 1,2-DIEN-4-OLS USING CHIRAL TIN(IV) COMPLEXES CONTAINING DIETHYL TARTRATE AS AN AUXILIARY LIGAND [J].
BOLDRINI, GP ;
LODI, L ;
TAGLIAVINI, E ;
TARASCO, C ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5447-5452
[2]   A CONCISE CHEMICAL SYNTHESIS OF (+)-3-DEOXY-D-GLYCERO-D-GALACTO-NONULOSONIC ACID (KDN) [J].
CHAN, TH ;
LI, CJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (10) :747-748
[3]   Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].
Chan, TH ;
Yang, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229
[4]   1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].
CHAN, TH ;
LI, CJ ;
LEE, MC ;
WEI, ZY .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192
[5]  
CINTAS P, 1995, SYNLETT, P1087
[6]   INDIUM-MEDIATED ALLYLATIONS OF UNPROTECTED CARBOHYDRATES IN AQUEOUS-MEDIA - A SHORT SYNTHESIS OF SIALIC-ACID [J].
GORDON, DM ;
WHITESIDES, GM .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7937-7938
[7]   Enantioselective allylation of alpha-ketoester oximes with an external chiral ligand: Asymmetric synthesis of allylglycines and allylalanine [J].
Hanessian, S ;
Yang, RY .
TETRAHEDRON LETTERS, 1996, 37 (50) :8997-9000
[8]  
Hong BC, 1998, ANGEW CHEM INT EDIT, V37, P468, DOI 10.1002/(SICI)1521-3773(19980302)37:4<468::AID-ANIE468>3.0.CO
[9]  
2-Z
[10]  
HONG BC, 1998, ANGEW CHEM, V110, P482