Diastereoselective temporary silicon-tethered ring-closing-metathesis reactions with prochiral alcohols: A new approach to long-range asymmetric induction

被引:56
作者
Evans, PA [1 ]
Cui, B
Buffone, GP
机构
[1] Indiana Univ, Dept Chem, Bloomington, IN 47405 USA
[2] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA
关键词
cyclization; diastereoselectivity; medium-sized rings; metathesis; silicon;
D O I
10.1002/anie.200250486
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A useful approach to 1,4-, 1,5-, and 1,6-stereocontrol, diastereoselective ring-closing-metathesis reactions that utilize temporary silicon tethers represent a new strategy for long-range asymmetric induction. This method facilitates the construction of cis-1,4-silaketals (n = 0, d.r. = 20:1; see scheme), whereas the extension of this concept to higher alkenyl alcohols (n = 1-4) results in a reversal of diastereoselectivity that favors formation of the trans isomer.
引用
收藏
页码:1734 / 1737
页数:4
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