Synthesis of α,β-Unsaturated Acylsilanes via Perrhenate-Catalyzed Meyer-Schuster Rearrangement of 1-Silyialkyn-3-ols

被引：21

作者：

Nikolaev, Andrei ^{[1
]}

Orellana, Arturo ^{[1
]}

机构：

[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 23期

基金：

加拿大自然科学与工程研究理事会;

关键词：

PARA-TOLUENESULFONIC ACID; ALLYLIC ALCOHOLS; SILYL ETHERS; TETRABUTYLAMMONIUM PERRHENATE(VII); ORGANIC-SYNTHESIS; ACYL SILANES; ISOMERIZATION; 1,3-ISOMERIZATION; DERIVATIVES; COMPLEXES;

D O I：

10.1021/acs.orglett.5b02909

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the synthesis of alpha,beta-unsaturated acylsilanes via the perrhenate-catalyzed Meyer-Schuster rearrangement of 1-silylalkyn-3-ols. Propargylic alcohols derived from TES-acetylene and substituted benzaldehydes can be converted to acylsilanes using a combination of p-TSA. H2O and n-Bu4N center dot ReO4, or Ph3SiOReO3 in good yields. Some propargylic alcohols derived from ketones, as well as aliphatic and unsaturated aldehydes, can also be converted to acylsilanes; however, they were often prone to side reactions.

引用

页码：5796 / 5799

页数：4

共 30 条

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