Highly Efficient Desymmetrization of Glutaric Anhydrides

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.