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Synthesis 2016; 48(10): 1474-1482
DOI: 10.1055/s-0035-1560420
DOI: 10.1055/s-0035-1560420
paper
Squaramide-Catalyzed Michael Addition as a Key Step for the Direct Synthesis of GABAergic Drugs
Further Information
Publication History
Received: 26 November 2015
Accepted after revision: 05 February 2016
Publication Date:
11 March 2016 (online)
Abstract
Enantioselective organocatalytic Michael additions serve as the key step in syntheses of chiral drugs based on γ-aminobutyric acid. The applicability of various squaramide catalysts for these Michael-type reactions has been assessed. Very good results in terms both activity and enantioselectivity were obtained in the Michael addition of dimethyl malonate to β-nitrostyrenes. On the other hand, a complementary approach, the addition of nitromethane to cinnamaldehydes, worked well with a squaramide catalyst possessing an adjacent pyrrolidine moiety. The corresponding Michael adducts obtained in the best conditions are suitable chiral intermediates for the synthesis of therapeutically useful GABA derivatives. Polymer-immobilized squaramides afforded the Michael adduct in high enantiomeric purity, but yield deterioration was observed between runs. Two different formal total syntheses of baclofen have also been accomplished.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560420.
- Supporting Information
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