INTERMOLECULAR ALDOL REACTIONS VIA ALLYLIC O-STANNYL KETYLS

被引：13

作者：

ENHOLM, EJ

WHITLEY, PE

机构：

[1] Department of Chemistry, University of Florida, Gainesville

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(95)01999-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and neutral free radical reaction of an alpha,beta-unsaturated ketone and tributyltin radical produced a resonance-stabilized allylic O-stannyl ketyl intermediate. A tin(IV) enolate, produced by subsequent hydrogen atom transfer, was next quenched with various aldehydes to yield an aldol product which was readily eliminated with p-toluenesulfonic acid to afford new alpha,beta-unsaturated ketones with E/Z ratios up to >100:1.

引用

页码：9157 / 9160

页数：4

共 18 条

[1] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].