4-Benzyl-2,3-didehydroprolinate as a homochiral template for Michael additions. Synthesis of enantiopure alpha-allokainoids, beta-Kainoids, 2,3-methanoprolines and other 3,4-disubstituted prolines

被引：26

作者：

Ezquerra, J

Escribano, A

Rubio, A

Remuinan, MJ

Vaquero, JJ

机构：

[1] CTR INVEST LILLY SA,VALDEOLMOS 28130,MADRID,SPAIN

[2] UNIV ALCALA DE HENARES,DEPT QUIM ORGAN,ALCALA DE HENARES 28871,MADRID,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 09期

关键词：

D O I：

10.1016/0957-4166(96)00336-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ethyl (4R)-N-methoxycarbonyl-4-benzyl-2,3-didehydroprolinate 10a undergoes Michael additions with stabilized carbanions and cuprates giving exclusively the enantiopure all-trans 3,4-disubstituted prolinates. The high stereoselection observed in this reaction is driven by the C-4 substituent of the Michael acceptor. This methodology has been applied to the synthesis of the enantiopure beta-kainoid 5a and the 2,3-methanoproline 15. Copyright (C) 1996 Elsevier Science Ltd

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页码：2613 / 2626

页数：14

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