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Synfacts 2011(8): 0881-0881  
DOI: 10.1055/s-0030-1260818
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Scandium-Catalyzed Asymmetric Sulfa-Michael Addition in Water

Contributor(s): Hisashi Yamamoto, Zhi Li
S. Bonollo, D. Lanari, F. Pizzo, L. Vaccaro*
Università di Perugia, Italy
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

This report describes a highly enantioselective Lewis acid catalyzed sulfa-Michael ­addition reaction of thiols to α,β-unsaturated ­ketones. The Lewis acid is scandium(III) triflate and the chiral ligand is a chiral bipyridine. Interestingly, water is found to be the best choice of solvent, which makes this process environmentally benign.