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Synfacts 2006(9): 0953-0953  
DOI: 10.1055/s-2006-949227
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Addition of 1,3-Dicarbonyl Compounds to Maleimides

Contributor(s): Benjamin List, Subhas Chandra Pan
G. Bartoli*, M. Bosco, A. Carlone, A. Cavalli, M. Locatelli, A. Mazzanti, P. Ricci, L. Sambri, P. Melchiorre*
University of Bologna, Italy
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Publikationsdatum:
23. August 2006 (online)

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Significance

Here the authors report an asymmetric direct conjugate addition of 1,3-dicarbonyl compounds to maleimides. Natural cinchona alkaloids quinine or quinidine have been found to be effective for the reaction. With 10-20 mol% of quinine or quinidine both high enantioselectivities (91:9-99:1 er) and diastereoselectivities (84:16 to 98:2 dr) are obtained for different β-keto esters and β-diketones.