Synfacts 2010(12): 1423-1423  
DOI: 10.1055/s-0030-1258921
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient Desymmetrization of Glutaric Anhydrides

Contributor(s): Benjamin List, Ji-Woong Lee
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.