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Synlett 2004(13): 2425-2428  
DOI: 10.1055/s-2004-832839
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© Georg Thieme Verlag Stuttgart · New York

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;
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Publication History

Received 15 June 2004
Publication Date:
24 September 2004 (online)

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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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