Rate Limiting Step Precedes C-C Bond Formation in the Archetypical Proline-catalyzed Intramolecular Aldol Reaction

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2009 Feb 5

PMID 19191687

Citations 11

Authors

Hui Zhu

Fernando R Clemente

K N Houk

Matthew P Meyer

Affiliations

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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.

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