Stereoselective synthesis of tetrahydropyrans via formal [4+2]-cycloaddition: A comparison of allylsilane and crotylsilane

被引：14

作者：

Angle, SR ^{[1
]}

Belanger, DS ^{[1
]}

El-Said, NA ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 22期

关键词：

D O I：

10.1021/jo0203342

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of a series of beta-(triethylsilyloxy)aldehydes with several allylsilanes and crotyldimethylphenylsilane is described. Aldehydes possessing an alpha-stereocenter afforded tetrahydropyrans as mixtures of two diastereomers with allylsilane, but only a single diastereomer was observed in the case of crotylsilanes. The reaction time for crotylsilanes was longer than that for allylsilanes likely due to the increased steric hindrance. Allylsilanes afforded tetrahydropyrans in 34-67% yields, and crotylsilanes provided products in 0-62% yields.

引用

页码：7699 / 7705

页数：7

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