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, 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.