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

Christoph Bornschein, Alastair J.J. Lennox, Svenja Werkmeister, Kathrin Junge, Matthias Beller

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

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 β-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.

Original languageEnglish
Pages (from-to)1915-1919
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number9
DOIs
StatePublished - Mar 2015
Externally publishedYes

Keywords

  • Azetidines
  • Hydrosilylation
  • Lactams
  • Reduction
  • Rhodium

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