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4-Fluoro and 4-Hydroxy Pyrrolidine-thioxotetrahydropyrimidinones: Organocatalysts for Green Asymmetric Transformations in Brine

Nikolaos Kaplaneris, Giorgos Koutoulogenis, Marianna Raftopoulou and Christoforos G. Kokotos*

*Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece, Email: ckokotoschem.uoa.gr

N. Kaplaneris, G. Koutoulogenis, M. Raftopoulou, C. G. Kokotos, J. Org. Chem., 2015, 80, 5464-5473.

DOI: 10.1021/acs.joc.5b00283 (free Supporting Information)


 

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Abstract

Pyrrolidinine-thioxotetrahydropyrimidinone derivatives were tested for their catalytic properties in various asymmetric organic transformations. These catalysts could efficiently catalyze the reactions in brine, without the use of organic solvent, and by employing an almost stoichiometric amount of reagents. Thus, the products were isolated by simple extractions in excellent yields, diastereoselectivities, and enantioselectivities.

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Key Words

1,4-addition, cyclohexanones, organocatalysis, green chemistry


ID: J42-Y2015