Copper(II)-Catalyzed Silylation of Activated Alkynes in Water: Diastereodivergent Access to E- or Z-β-Silyl-α,β-Unsaturated Carbonyl and Carboxyl Compounds.

Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2PhSiBpin in water at room temperature and open atmosphere, vinylsilanes conjugated to carbonyl groups are synthesized in high yield. A surprising diastereodivergent access to olefin geometry was discovered using a silyl conjugate addition strategy: aldehydes and ketones were Z selective while esters and amides were exclusively transformed into the E products. [ABSTRACT FROM AUTHOR]