Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynska dolina CH-2, SK-842 15 Bratislava, Slovakia
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Org. Biomol. Chem., 2013,11, 7705-7711
21 Aug 2013,
20 Sep 2013
First published online
24 Sep 2013
Asymmetric organocatalytic 1,4-additions provide access to a large number of biologically relevant compounds. Chiral squaramides efficiently catalyse enantioselective Michael addition of 1,3-dicarbonyl compounds to aliphatic nitroalkenes. The resulting γ-nitro carboxylic derivatives were obtained in high yields and in high enantiomeric purities. Quantum chemical calculations helped us to devise a transition state model, which explains the observed stereochemical course of the addition. The best results were obtained with Meldrum's acid as a donor, with which enantiomeric purity of the Michael adduct was 97:3 e.r. Using this methodology pregabalin was synthesized in three steps in overall 52% yield.
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Organic & Biomolecular Chemistry
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