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Highly Enantioselective Organocatalytic Sulfa-Michael Addition to α,β-Unsaturated Ketones

Nirmal K. Rana, Sermadurai Selvakumar and Vinod K. Singh*

*Department of Chemistry, Indian Institute of Technology, Kanpur, India 208 016, Email:

N. K. Rana, S. Selvakumar, V. K. Singh, J. Org. Chem., 2010, 75, 2089-2091.

DOI: 10.1021/jo902634a


A cinchona alkaloid-derived urea is an efficient organocatalyst for catalyzing enantioselective conjugate addition between thiols and various α,β-unsaturated ketones to provide optically active sulfides with high chemical yields and enantiomeric excess. The reaction was performed with 0.1 mol % of catalyst in toluene at room temperature.

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Key Words

β-sulfido carbonyl compounds, aryl sulfides, organocatalysis

ID: J42-Y2010-0780