Remote stereocontrol using allylstannanes: reversal in stereoselectivity using indium(III) and bismuth(III) halides as promoters

被引：31
|
作者：
Donnelly, S
Thomas, EJ
Arnott, EA
机构：
[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England
[2] AstraZeneca, Macclesfield SK10 2NA, Cheshire, England
来源：
CHEMICAL COMMUNICATIONS | 2003年 / 12期
关键词：
D O I：
10.1039/b303151a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Allyl-indium(III) and -bismuth(III) dihalides, generated by transmetallation of 5-benzyloxy-4-methylpent-2-enyl(tributyl)stannane 1, react with aldehydes with useful levels of 1,5-stereocontrol, a 93 : 7 ratio of 1,5-epimers in favour of the 1,5-anti-(E)-stereoisomers 7 and 11 typically being obtained using bismuth( III) iodide. The 4-benzyloxypent-2-enylstannane 4 similarly gives the 1,5-syn-(E)-hex-3-enols 13 also with ca. 93 : 7, stereoselectivity.
引用
收藏
页码：1460 / 1461
页数：2
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