Rate limiting step precedes C-C bond formation in the archetypical proline-catalyzed intramolecular aldol reaction.
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.
Zhu
Hui
H
University of California, Merced, School of Natural Sciences, P.O. Box 2039, Merced, California 95344, USA.
Clemente
Fernando R
FR
Houk
K N
KN
Meyer
Matthew P
MP
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D011392:Proline
D001643:Bridged Bicyclo Compounds; D007659:Ketones; D011392:Proline