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*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

15 Citations (Scopus)

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. A selective Rh-catalyzed protocol to reduce β-lactams to important pharmacologically active azetidines is presented. Reaction with 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 high synthetic utility of this procedure.

Original languageEnglish
Pages (from-to)1915-1919
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number9
DOIs
Publication statusPublished - 1 Jan 2015

Keywords

  • Azetidines
  • Hydrosilylation
  • Lactams
  • Reduction
  • Rhodium

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