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Synfacts 2010(12): 1423-1423
DOI: 10.1055/s-0030-1258921
DOI: 10.1055/s-0030-1258921
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Highly Efficient Desymmetrization of Glutaric Anhydrides
S. E. Park, E. H. Nam, H. B. Jang, J. S. Oh, S. Some, Y. S. Lee, C. E. Song*
Sungkyunkwan University, Suwon, Korea
Further Information
Publication History
Publication Date:
22 November 2010 (online)
Significance
The authors report a highly efficient desymmetrization of glutaric anhydrides by the cinchona-based sulfonamide catalyst 1. The obtained 3-substituted glutaric hemiesters can be easily converted into valuable chiral synthons, such as HMG-CoA reductase inhibitors (statins), baclofen, pregabalin, and paroxetine. Extensive screening of bifunctional cinchona-based catalysts revealed that sulfonamide-derived catalyst 1 showed superior reactivity and enantioselectivity than thiourea- and squaramide-based catalysts.