Bispidine-derived N-acyliminium ions in synthesis:: stereocontrolled construction of the BCD rings of sparteine

被引：22

作者：

Harrison, JR ^{[1
]}

O'Brien, P ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 32期

关键词：

diamines; iminium salts; Grignard reagents; bicyclic heterocyclic compounds;

D O I：

10.1016/S0040-4039(00)00999-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of Grignard reagents with bispidine-derived N-acyliminium ions (generated in situ from an alpha-methoxy bispidine amide) has been studied as a new route to sparteine analogues. The addition reactions proceed with complete diastereoselectivity to generate products with the same relative stereochemistry as in the BCD rings of sparteine. The first stereocontrolled synthesis of a tricyclic diamine structurally equivalent to the BCD rings of sparteine, is described. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：6167 / 6170

页数：4

共 24 条

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