Influence of the Diene in the Hetero-Diels-Alder Reaction Catalyzed by Dirhodium(II) Carboxamidates

Marcela Valenzuela; Michael P. Doyle; Christine Hedberg; Wenhao Hu; Alexandra Holmstrom

doi:10.1055/s-2004-832839

CLUSTER

Influence of the Diene in the Hetero-Diels-Alder Reaction Catalyzed by Dirhodium(II) Carboxamidates

Marcela Valenzuela, Michael P. Doyle*, Christine Hedberg, Wenhao Hu, Alexandra Holmstrom
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA
Fax: +1(301)3149121; e-Mail: mdoyle3@umd.edu;

Abstract

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Abstract

Chiral dirhodium(II) carboxamidates catalyze highly stereoselective hetero-Diels-Alder reactions of aromatic aldehydes with methyl-substituted Danishefsky’s dienes with high turnover numbers. The methyl substituents of the diene influence both enantioselectivity in product formation and the rate of the reaction in the presence of chiral dirhodium(II) Lewis acids.

Key words

hetero-Diels-Alder reaction - catalytic asymmetric synthesis - chiral Lewis acids - dirhodium(II) carboxamidates - cycloaddition

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Referenzen

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