Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions

Natalia Zotova, Linda J. Broadbelt, Alan Armstrong, Donna G. Blackmond*

*Corresponding author for this work

Research output: Contribution to journalArticle

57 Scopus citations

Abstract

Reaction progress kinetic analysis of the proline-mediated intermolecular aldol reaction shows that the rate depends on the concentrations of both the donor ketone1 and the electrophilic aldehyde 2, implying that enamine formation cannot be rate-determining. The observed kinetics and deuterium isotope effects are consistent with formation of the product iminium species as the rate-determining step.

Original languageEnglish (US)
Pages (from-to)3934-3937
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number14
DOIs
StatePublished - Jul 15 2009

Keywords

  • Asymmetric catalysis
  • Kinetics
  • Mechanism
  • Organocatalysis
  • Proline

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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