Generation of (E)-silylketene acetals in a Rhodium-DuPhos catalyzed two-step reductive aldol reaction.
[reaction: see text]. Mechanistic studies employing in situ NMR analysis implicate intermediate silicon enolates as reactive intermediates in the Rh-DuPhos catalyzed two-step reductive aldol reaction with Cl(2)MeSiH. These enolates undergo noncatalyzed reaction with a variety of aldehydes to give the derived syn-aldol adduct in high yields and diastereoselection.
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Department of Chemistry, Venable and Kenan Laboratories, The University of North Carolina at Chapel Hill, 27599-3290, USA.
Bass
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Morken
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JP