Regio- and stereoselective Heck arylations of N-carbomethoxy-L-3-dehydroproline methyl ester with arenediazonium salts.: Total synthesis of neuroexcitatory aryl kainoids

被引：30

作者：

da Silva, Kezia Peixoto ^{[1
]}

Godoi, Marla Narciso ^{[1
]}

Duarte Correia, Carlos Roque ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, UNICAMP, BR-13084971 Campinas, SP, Brazil

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 15期

关键词：

D O I：

10.1021/ol070980t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Heck arylation of N-carbomethoxy-(L)-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.

引用

页码：2815 / 2818

页数：4