Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 16, Pages 4154-4158Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310695
Keywords
copper; diastereoselectivity; heterogeneous catalysis; silicon; water chemistry
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Funding
- ACS Petroleum Research Fund
- NIH [NIGMS RO1 GM093834]
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Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me(2)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 Eproducts.
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