4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 5, Pages 1632-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja806672y

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Funding

  1. NIH-NIHGMS [GM-36700]

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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 C-13 kinetic isotope effects for this reaction show conclusively that carbon-carbon bond formation is not rate-limiting.

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