A CONVERGENT METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALKENES

被引:41
作者
MARTIN, SF
DANIEL, D
CHERNEY, RJ
LIRAS, S
机构
[1] Department of Chemistry and Biochemistry, University of Texas, Austin
关键词
D O I
10.1021/jo00035a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.
引用
收藏
页码:2523 / 2525
页数:3
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