Diastereoselective Oxidative Carbon-Carbon Bond Formation via Silyl Bis-enol Ethers

被引:54
作者
Avetta, Christopher T., Jr. [1 ]
Konkol, Leah C. [1 ]
Taylor, Carla N. [1 ]
Dugan, Karen C. [1 ]
Stern, Charlotte L. [1 ]
Thomson, Regan J. [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1021/ol802516z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.
引用
收藏
页码:5621 / 5624
页数:4
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