Stereocontrolled synthesis of 5-acyl-3,4-dihydro-2H-pyrroles and related heterocycles via intramolecular 2-propylidene-1,3-bis(silane)-acylnitrilium ion cyclizations

被引：21

作者：

Kercher, T ^{[1
]}

Livinghouse, T ^{[1
]}

机构：

[1] MONTANA STATE UNIV,DEPT CHEM & BIOCHEM,BOZEMAN,MT 59717

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 04期

关键词：

D O I：

10.1021/jo961452q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Propylidene-1,3-bis(silane)s have been shown to be highly effective terminators in heteroannulations initiated by C-acylnitrilium ions. These cyclizations proceed under exceedingly mild reaction conditions with good to excellent levels of substrate-derived stereocontrol to provide the corresponding Delta(1)-pyrrolines possessing a functionalizable allylsilane moiety. Sequential reduction/N-tosylation of these products leads to the stereoselective formation of cis-pyrrolidine derivatives.

引用

页码：805 / 812

页数：8

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