Tributyltin hydride-mediated radical cyclisation of aldehydes and unsaturated ketones: the synthesis of hydroxy tetrahydrofurans, chromanols and related compounds

被引：20

作者：

Bebbington, D

Bentley, J

Nilsson, PA

Parsons, AF ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] Vernalis Res Ltd, Wokingham RG41 5UA, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 46期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclisation; oxygen heterocycles; radicals and radical reactions; tin and compounds;

D O I：

10.1016/S0040-4039(00)01586-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tributyltin hydride-mediated cyclisation of unsaturated ethers bearing an aldehyde or alpha,beta -unsaturated ketone group is reported. Cyclisation proceeds via addition of the tributyltin radical to the carbonyl double bond and the resultant O-stannyl ketyl can add intramolecularly to electron-rich double bonds to form hydroxy tetrahydrofurans, chromanols or related compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8941 / 8945

页数：5

共 14 条

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GOMIS M, 1988, B SOC CHIM FR, P585

[12] COMPARISON OF STEREOSELECTIVITY OF INTRAMOLECULAR CYCLIZATION OF ALDEHYDES TETHERED WITH CONJUGATED ESTERS INDUCED BY O-STANNYL AND O-SAMARIUM KETYLS TO FORM THE TETRAHYDROFURAN RING-SYSTEMS [J].