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The Origin of Stereoselectivity in Primary Amino Acid Catalyzed Intermolecular Aldol Reactions
Author(s) -
Bassan Arianna,
Zou Weibiao,
Reyes Efraim,
Himo Fahmi,
Córdova Armando
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502388
Subject(s) - cyclohexanone , aldol reaction , intermolecular force , enamine , chemistry , stereoselectivity , catalysis , benzaldehyde , primary (astronomy) , transition state , stereochemistry , computational chemistry , organic chemistry , molecule , physics , astronomy
Combined forces : Theory and experiment are used together to determine the mechanism of primary amino acid catalyzed intermolecular aldol reactions. A six‐membered chairlike structure is determined to be the transition state for the reaction between benzaldehyde and cyclohexanone catalyzed by ( S )‐alanine (see scheme), and a carboxylic acid catalyzed enamine mechanism is shown to be the most favorable reaction pathway.