N-(SILYLMETHYL)-SUBSTITUTED KETENE N,S-ACETALS AS A SYNTHETIC EQUIVALENT OF NOVEL 1,3-DIPOLAR REAGENT, ALKYLIDENEAZOMETHINE YLIDES - SYNTHESIS AND [3+2]-CYCLOADDITIONS

被引：35

作者：

HOSOMI, A ^{[1
]}

MIYASHIRO, Y ^{[1
]}

YOSHIDA, R ^{[1
]}

TOMINAGA, Y ^{[1
]}

YANAGI, T ^{[1
]}

HOJO, M ^{[1
]}

机构：

[1] NAGASAKI UNIV,FAC PHARMACEUT SCI,NAGASAKI 852,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 19期

关键词：

D O I：

10.1021/jo00306a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: A variety of N-(silylmethyl)-substituted ketene N,S-acetals, readily prepared by the reaction of ketene dithioacetals with ((trimethylsilyl)methyl)amine, followed by N-alkylation, react smoothly with activated alkenes, carbonyl compounds, and thioketones, to afford α-alkylidenepyrrolidines, oxazolidines, and thiazolidines, via a 1,3-elimination of (methylthio)trimethylsilane. These reagents are synthetic equivalents of alkylideneazomethine ylids. © 1990, American Chemical Society. All rights reserved.

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页码：5308 / 5310

页数：3

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