The "Aqueous" prins reaction

被引：40

作者：

Aubele, DL ^{[1
]}

Lee, CA ^{[1
]}

Floreancig, PE ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 23期

关键词：

D O I：

10.1021/ol0359259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this communication we demonstrate that Prins cyclization reactions occur under very mild conditions when cyclic alpha,beta-unsaturated acetals are employed as oxocarbenium ion progenitors and allylsilanes are used as nucleophiles. Cyclizations proceed efficiently inside Lewis acidic micelles in water, demonstrating that colloidal suspensions can protect highly electrophilic intermediates from hydrolysis. Reactions are experimentally facile and useful in the preparation of a variety of vinyl- and aryl-substituted tetrahydropyrans with excellent stereocontrol.

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页码：4521 / 4523

页数：3

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