title: 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.
authors.affiliation: University of California, Merced, School of Natural Sciences, P.O. Box 2039, Merced, California 95344, USA.
authors.forename: Hui
authors.initials: H
authors.lastname: Zhu
authors.forename: Fernando R
authors.initials: FR
authors.lastname: Clemente
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Matthew P
authors.initials: MP
authors.lastname: Meyer
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D011392:Proline
chemical_list: D001643:Bridged Bicyclo Compounds; D007659:Ketones; D011392:Proline