The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: synthesis of (Z)-dienes

被引：6
|
作者：
Barlan, Allan U. [1 ]
Micalizio, Glenn C. [1 ]
机构：
[1] Scripps Florida, Scripps Res Inst, Dept Chem, Jupiter, FL 33458 USA
来源：
TETRAHEDRON | 2010年 / 66卷 / 26期
基金：
美国国家卫生研究院;
关键词：
Allenes; Titanium; Reductive Cross-Coupling; Z-dienes; BOND-FORMING HYDROGENATION; ALPHA-HYDROXY ESTERS; ALLYLIC ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; ETHYLMAGNESIUM BROMIDE; IMINE VINYLATION; CATALYZED HOMOALLYLATION; SUBSTITUTED 1,4-DIENES; 3+2 CYCLOADDITION; TERMINAL ALLENES;
D O I：
10.1016/j.tet.2010.02.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In investigations aimed at exploring the potential of disubstituted allenes in stereoselective synthesis, we report studies that explore the reductive cross-coupling reaction of vinylsilanes with a range of substituted allenes. Regiochemical control is attained by employing allenic alkoxides, where the proximal heteroatom dictates the site-selectivity in a process that proceeds by net formal metallo-[3,3] rearrangement (directed carbometalation/elimination). Stereoselectivity in these reactions is complex, with both the nature of allene substitution and relative stereochemistry of the substrate impacting the stereoselective generation of each alkene of a substituted 1,3-diene. (C) 2010 Published by Elsevier Ltd.
引用
收藏
页码：4775 / 4783
页数：9
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