A Highly Reactive and Enantioselective Bifunctional Organocatalyst for the Methanolytic Desymmetrization of Cyclic Anhydrides: Prevention of Catalyst Aggregation

Unprecedented reactivity and high stereoselectivity were observed in the ring opening of meso anhydrides under mild conditions with a cinchona-alkaloid-based sulfonamide catalyst (see scheme). Computation of the catalyst–transition-state analogue (right; gray C, white H, green F, blue N, red O, yellow S) provided insight into the origin of the stereoselectivity.