Rate limiting step precedes C-C bond formation in the archetypical proline-catalyzed intramolecular aldol reaction

J Am Chem Soc. 2009 Feb 11;131(5):1632-3. doi: 10.1021/ja806672y.

Abstract

The archetypical proline-catalyzed intramolecular aldol reaction, the Hajos-Parrish-Eder-Sauer-Wiechert reaction, has served as a model reaction for the mechanistic study of the ever-growing class of proline-catalyzed conversions. Experimental measurements of the (13)C kinetic isotope effects for this reaction show conclusively that carbon-carbon bond formation is not rate-limiting.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis
  • Catalysis
  • Cyclization
  • Ketones / chemical synthesis
  • Ketones / chemistry*
  • Kinetics
  • Proline

Substances

  • Bridged Bicyclo Compounds
  • Ketones
  • Proline