Hydrogen bonding catalysis operates by charge stabilization in highly polar diels - Alder reactions

Ruth Gordillo, Travis Dudding, Christopher D. Anderson, K. N. Houk

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

The alcohol-catalyzed Diels - Alder reactions of acrolein and benzaldehyde with Rawal's diene were evaluated with density functional theory (B3LYP/6-31G(d)). Several potential modes of catalysis with two methanol molecules were used to model catalysis by TADDOLs. In agreement with crystallographic data, cooperative catalysis with TADDOLs is predicted to be favorable.

Original languageEnglish (US)
Pages (from-to)501-503
Number of pages3
JournalOrganic Letters
Volume9
Issue number3
DOIs
StatePublished - Feb 1 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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