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

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posted on 2008-12-18, 00:00 authored by Christopher T. Avetta, Leah C. Konkol, Carla N. Taylor, Karen C. Dugan, Charlotte L. Stern, Regan J. Thomson
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.