Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.
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.
Gutierrez
Osvaldo
O
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Iafe
Robert G
RG
Houk
K N
KN
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
D003517:Cyclopentanes; D048289:Imidazolidines; D007659:Ketones