Stereospecific synthesis of cis-2-alkoxy-3-aminooxolanes

被引：8

作者：

DeKimpe, N ^{[1
]}

Aelterman, W ^{[1
]}

DeGeyter, K ^{[1
]}

Declercq, JP ^{[1
]}

机构：

[1] UNIV CATHOLIQUE LOUVAIN,CHIM PHYS & CRISTALLOG LAB,B-1348 LOUVAIN,BELGIUM

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 15期

关键词：

D O I：

10.1021/jo970410e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis-2-Alkoxy-3-aminooxolanes 4 were synthesized in a remarkably stereospecific manner by alcoholysis of alpha-chloro-gamma-((trimethylsilyl)oxy)ketimines 2, obtained by alkylation of alpha-chloroketimines 1 with 2-bromo-1-((trimethylsilyl)oxy)ethane. The stereospecificity of the cyclization was lost when the alcoholysis was performed in the presence of base. However, complete transformation of the mixtures of cis- and trans-2-alkoxy-3-aminooxolanes into the more stable cis-compounds was achieved with hydrogen chloride in methanol. A mechanistic rationale for these stereochemical aspects is presented.

引用

页码：5138 / 5143

页数：6

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