Pyrrolidine-thioxotetrahydropyrimidinone as an efficient organocatalyst for the enantioselective Michael addition of cyclic ketones to nitrodienes |
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Authors: | Michail Tsakos Maria Trifonidou Christoforos G. Kokotos |
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Affiliation: | Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, 15771 Athens, Greece |
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Abstract: | Among the various Michael additions, the enantioselective reaction between cyclic ketones and nitrodienes has received little attention in comparison to the corresponding reaction with nitroolefins. A bifunctional organocatalyst consisting of the pyrrolidine moiety and a thioxotetrahydropyrimidinone ring successfully catalyzed this asymmetric transformation. The products of the reaction between various ketones and nitrodienes were obtained in high yields (up to 96%) with excellent diastereo- (up to >98:2 dr) and enantioselectivities (up to 99:1% er). |
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