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Copper(II)-catalyzed silylation of activated alkynes in water: diastereodivergent access to E- or Z-?-silyl-?,?-unsaturated carbonyl and carboxyl compounds.

ABSTRACT: Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2 PhSiBpin 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.

SUBMITTER: Calderone JA

PROVIDER: S-EPMC4035118 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature

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Copper(II)-catalyzed silylation of activated alkynes in water: diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds.

Calderone Joseph A JA Santos Webster L WL

Angewandte Chemie (International ed. in English) 20140214 16

Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2 PhSiBpin 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. ...[more]

PMID: 24532188

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