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
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
收藏
页码:5796 / 5799
页数:4
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