Intramolecular cycloaddition reactions of silyl nitronate tethered to vinylsilyl group: 2-nitroalkanols as precursors for amino polyols

被引：25

作者：

Kudoh, T ^{[1
]}

Ishikawa, T

Shimizu, Y

Saito, S

机构：

[1] Okayama Univ, Sch Engn, Dept Biosci & Biotechnol, Okayama 7008530, Japan

[2] Okayama Univ, Sch Educ, Okayama 7008530, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol035423v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et3N in CH3CN at 0 degreesC to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2] cycloaddition reaction. Some examples for transforming the cycloadducts to amino polyols are also presented.

引用

页码：3875 / 3878

页数：4

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