Highly Enantioselective Catalytic Thiolysis of Prochiral Cyclic Dicarboxylic Anhydrides Utilizing a Bifunctional Chiral Sulfonamide

摘要

Asymmetric differentiation between two identical carbonyl groups of prochiral sigma-symmetric dicarboxylic acid derivatives by using an enzymatic or a nonenzymatic procedure is a rational and useful strategy for the asymmetric synthesis of biologically active compounds and medicines. The resultant chiral products can be subjected to further so-called "enan-tioconvergent" and "enantiodivergent" transformations on the basis of latent sigma symmetry.Previously,we disclosed remarkable nonenzymatic asymmetric induction methods for various prochiral o-symmetric dicarboxylic acid derivatives based on highly diastereoselective aminolysis and Die-ckmann-type cyclizations using functional heterocycles,such as the C4-chiral l,3-thiazolidine-2-thiones.