A Mild and Selective Reduction of [beta]-Lactams: Rh-Catalyzed Hydrosilylation towards Important Pharmacological Building Blocks

Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary [beta]-lactams. Reaction with the tertiary amides was selective over secondary amides, esters, olefi...

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Published inEuropean journal of organic chemistry Vol. 2015; no. 9; p. 1915
Main Authors Bornschein, Christoph, Lennox, Alastair J J, Werkmeister, Svenja, Junge, Kathrin, Beller, Matthias
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.03.2015
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Summary:Four-membered N-heterocyclic compounds exhibit a broad range of pharmacological activities. Herein, we report a useful rhodium-catalyzed protocol for the activation of phenylsilane to reduce tertiary [beta]-lactams. Reaction with the tertiary amides was selective over secondary amides, esters, olefins and nitriles, with no erosion of stereochemistry. A one-pot protocol from commercially available starting materials and a selective reduction of a complex penicillin derivative demonstrate the synthetic utility of this facile procedure.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403655