STEREOSELECTIVE 1,4-HYDROBORATION OF ACYCLIC (E)-ALPHA,BETA-UNSATURATED KETONES WITH DIALKYLBORANES - SYNTHESIS OF (Z)-VINYLOXYBORANES

被引：13

作者：

BOLDRINI, GP ^{[1
]}

BORTOLOTTI, M ^{[1
]}

TAGLIAVINI, E ^{[1
]}

TROMBINI, C ^{[1
]}

UMANIRONCHI, A ^{[1
]}

机构：

[1] UNIV BOLOGNA,DIPARTIMENTO CHIM GIACOMO CIAMICIAN,VIA SELMI 2,I-40126 BOLOGNA,ITALY

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)92052-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dialkylboranes add to acyclic disubstituted (E)-alpha,beta-unsaturated ketones in a 1,4-fashion affording (Z)-vinyloxyboranes as major or sole products. The sterochemical outcome of the hydroboration reaction is consistent with a concerted pericyclic mechanism. The intermediate vinyloxyboranes can be trapped with aldehydes to give virtually pure syn beta-hydroxyketones.

引用

页码：1229 / 1232

页数：4

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