Stereocontrolled formation of spiro enones by radical cyclization of bromo acetals

被引：11

作者：

Clive, DLJ ^{[1
]}

Huang, XJ ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON | 2001年 / 57卷 / 18期

基金：

加拿大自然科学与工程研究理事会;

关键词：

spiro compounds; radical cyclization; enones;

D O I：

10.1016/S0040-4020(01)00226-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldol condensation of ketones with 2-[[(1,1-(dimethylethyl)diphenylsilyl]oxy]propanal (7), dehydration, NaBH4 reduction and treatment of the resulting alcohols with ethyl vinyl ether in the presence of NBS gives bromo acetals (e.g. 11) that undergo 5-exo-trigonal radical cyclization, affording compounds that are easily converted into spiro enones (e.g. 16). The stereochemistry at the spiro center is controlled by the stereochemistry at the hydroxyl-bearing carbon of the intermediate alcohol. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：3845 / 3858

页数：14

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