Enantioselective Enolate Protonation in Sulfa–Michael Addition to α-Substituted N-Acryloyloxazolidin-2-ones with Bifunctional Organocatalyst
- 18 November 2011
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 13 (24), 6520-6523
- https://doi.org/10.1021/ol202808n
Abstract
Organocatalytic conjugate addition of thiols to α-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules.Keywords
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