title: Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.
abstract: The organocatalytic transfer hydrogenation reactions of 3-phenyl-2-cyclopentenone with imidazolidinone catalysts are evaluated using the hybrid density functional (B3LYP/6-31G(d)) theory. The origin of the preference for the (E) iminium transition state is determined, and the stereoselectivity of hydride transfer is investigated.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Gutierrez
authors.forename: Robert G
authors.initials: RG
authors.lastname: Iafe
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D002384:Catalysis; D003198:Computer Simulation; D003517:Cyclopentanes / Q000737:chemistry; D006865:Hydrogenation; D048289:Imidazolidines / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D048289:Imidazolidines; D007659:Ketones