Issue 9, 2011

Novel pyrrolidine-thiohydantoins/thioxotetrahydropyrimidinones as highly effective catalysts for the asymmetric Michael addition

Abstract

The synthesis of novel organocatalysts consisting of a pyrrolidine moiety and a thiohydantoin or a thioxotetrahydropyrimidinone ring is described. The compound combining the pyrrolidine with the thioxotetrahydropyrimidinone was found to be a highly effective catalyst for the Michael reaction. Low catalyst loadings (1–2.5%) can be employed leading to quantitative yields and excellent stereoselectivities in the reaction between cyclic ketones and nitroolefins.

Graphical abstract: Novel pyrrolidine-thiohydantoins/thioxotetrahydropyrimidinones as highly effective catalysts for the asymmetric Michael addition

Supplementary files

Article information

Article type
Paper
Submitted
25 Nov 2010
Accepted
11 Feb 2011
First published
11 Feb 2011

Org. Biomol. Chem., 2011,9, 3386-3395

Novel pyrrolidine-thiohydantoins/thioxotetrahydropyrimidinones as highly effective catalysts for the asymmetric Michael addition

C. G. Kokotos, D. Limnios, D. Triggidou, M. Trifonidou and G. Kokotos, Org. Biomol. Chem., 2011, 9, 3386 DOI: 10.1039/C0OB01083A

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