title: Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.
abstract: Quantum mechanical calculations were employed to predict the ratio of four stereoisomeric products expected from two complex reactions involving the aldol reactions of cyclohexanone with benzaldehyde or with isobutyraldehyde catalyzed by (S)-proline. Experimental tests of these predictions provide an assessment of the state-of-the-art in quantum mechanical prediction of products of complex organic reactions in solution.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, USA.
authors.forename: S
authors.initials: S
authors.lastname: Bahmanyar
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
authors.forename: Harry J
authors.initials: HJ
authors.lastname: Martin
authors.forename: Benjamin
authors.initials: B
authors.lastname: List
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D008958:Models, Molecular; D011392:Proline / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000438:Alcohols; D000447:Aldehydes; D001547:Benzaldehydes; D003512:Cyclohexanones; C036468:cyclohexanone; D011392:Proline; C017439:isobutyraldehyde; C032175:benzaldehyde