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Synfacts 2008(2): 0199-0199  
DOI: 10.1055/s-2007-992439
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Michael Reactions of Dithiomalonates and β-Keto Thioesters

Contributor(s): Benjamin List, Subhas Chandra Pan
W. Ye, Z. Jiang, Y. Zhao, S. L. M. Goh, D. Leow, Y.-T. Soh, C.-H. Tan*
National University of Singapore, Republic of Singapore
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

The authors report enantioselective Michael reactions of dithiomalonates and β-keto thioesters using a range of acceptors, including maleimides, cyclic enones, furanone, and acyclic 1,4-dioxobutenes. Bicyclic chiral guanidine 1 acts as a versatile Brønsted base catalyst for this reaction. With 1-20 mol% of the catalyst 1 good to high yields (85-99%) and excellent enantioselectivities (er = 94:6 to 98:2) are obtained for different Michael acceptors.