The first enantioselective halo aldol reaction of ethyl propiolate and aldehydes

被引：28

作者：

Chen, DJ ^{[1
]}

Timmons, C ^{[1
]}

Liu, JY ^{[1
]}

Headley, A ^{[1
]}

Li, GG ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Biochem & Chem, Lubbock, TX 79409 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 15期

关键词：

aldol reactions; Morita-Baylis-Hillman esters; chiral salen; enantioselectivity;

D O I：

10.1002/ejoc.200400230

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first enantioselective halo aldol reaction of ethyl propiolate with aldehydes has been established by using Jacobsen's chiral cyclohexylsalen ligand. The reaction was conducted at -20degreesC in dichloromethane with Et(2)AII as the source of halogen and Lewis acid promoter. Excellent geometric selectivity (only the Z isomer) has been achieved for all 14 examples examined. The reaction works well with aromatic aldehydes; it also works with aliphatic aldehydes and alpha,beta-unsaturated aldehydes, albeit with diminished yields and ee. This method provides the first enantioselective synthesis of beta-iodo Morita-Baylis-Hillman (MBH) esters. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

引用

页码：3330 / 3335

页数：6

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