Attractive noncovalent interactions in asymmetric catalysis: Links between enzymes and small molecule catalysts

Robert R. Knowles, Eric N. Jacobsen

Research output: Contribution to journalArticle

435 Scopus citations

Abstract

Catalysis by neutral, organic, small molecules capable of binding and activating substrates solely via noncovalent interactions-particularly H-bonding-has emerged as an important approach in organocatalysis. The mechanisms by which such small molecule catalysts induce high enantioselectivity may be quite different from those used by catalysts that rely on covalent interactions with substrates. Attractive noncovalent interactions are weaker, less distance dependent, less directional, and more affected by entropy than covalent interactions. However, the conformational constraint required for high stereoinduction may be achieved, in principle, if multiple noncovalent attractive interactions are operating in concert. This perspective will outline some recent efforts to elucidate the cooperative mechanisms responsible for stereoinduction in highly enantioselective reactions promoted by noncovalent catalysts.

Original languageEnglish (US)
Pages (from-to)20678-20685
Number of pages8
JournalProceedings of the National Academy of Sciences of the United States of America
Volume107
Issue number48
DOIs
StatePublished - Nov 30 2010

All Science Journal Classification (ASJC) codes

  • General

Keywords

  • Enantioselectivity
  • H bonding
  • Organocatalysis
  • Transition state stabilization

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