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

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.

SUBMITTER: Zhu H

PROVIDER: S-EPMC3044651 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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

Zhu Hui H Clemente Fernando R FR Houk K N KN Meyer Matthew P MP

Journal of the American Chemical Society 20090201 5

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. ...[more]

PMID: 19191687

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