Download PDF
Synfacts 2008(5): 0499-0499  
DOI: 10.1055/s-2008-1072665
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cationic Dirhodium Carboxamidates for Lewis Acid Catalyzed Reactions

Contributor(s): Mark Lautens, Valentina Aureggi
Y. Wang, J. Wolf, P. Zavalij, M. P. Doyle*
University of Maryland, College Park, USA
Further Information

Publication History

Publication Date:
23 April 2008 (online)

    Permissions and Reprints

Significance

The development of a new class of cationic chiral dirhodium carboxamidates (Rh2 5+) to enhance the selectivity in Lewis acid catalyzed transformations is reported. Compared to the corresponding dirhodium(II) catalyst, the cationic Rh(II)/Rh(III) system increases the rate and enhances the stereocontrol of hetero-Diels-Alder reactions of aldehydes with Danishefsky’s diene and 1,3-dipolar cycloadditions of selected substrates. For previous reports, see: M. P. Doyle, I. M. Philips, W. Hu J. Am. Chem. Soc. 2001, 123, 5366; F. Viton, G. Bernardelli, E. P. Kündig J. Am. Chem. Soc. 2002, 124, 4968.