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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.

SUBMITTER: Gutierrez O

PROVIDER: S-EPMC2751814 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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Origin of stereoselectivity in the imidazolidinone-catalyzed reductions of cyclic alpha,beta-unsaturated ketones.

Gutierrez Osvaldo O Iafe Robert G RG Houk K N KN

Organic letters 20091001 19

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. ...[more]

PMID: 19722547

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