Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams

Dustin E.A. Raup, Benoit Cardinal-David, Dane Holte, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

324 Scopus citations

Abstract

Enzymes are a continuing source of inspiration for the design of new chemical reactions that proceed with efficiency, high selectivity and minimal waste. In many biochemical processes, different catalytic species, such as Lewis acids and bases, are involved in precisely orchestrated interactions to activate reactants simultaneously or sequentially. This type of 'cooperative catalysis', in which two or more catalytic cycles operate concurrently to achieve one overall transformation, has great potential in enhancing known reactivity and driving the development of new chemical reactions with high value. In this disclosure, a cooperative N-heterocyclic carbene/Lewis acid catalytic system promotes the addition of homoenolate equivalents to hydrazones, generating highly substituted γ-lactams in moderate to good yields and with high levels of diastereo- and enantioselectivity.

Original languageEnglish (US)
Pages (from-to)766-771
Number of pages6
JournalNature chemistry
Volume2
Issue number9
DOIs
StatePublished - Sep 2010

ASJC Scopus subject areas

  • General Chemistry
  • General Chemical Engineering

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