Journal
TETRAHEDRON LETTERS
Volume 53, Issue 16, Pages 2121-2124Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.02.052
Keywords
Organocatalyst; Thiourea; Sulfa-Michael; Thioacetic acid; alpha,beta-Unsaturated ketones
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Funding
- Department of Science and Technology, India
- Council of Scientific and Industrial Research (CSIR), New Delhi
- CSIR
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Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.
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