Stereoselective synthesis of 4-substituted-cyclic sulfamidate-5-carboxylates by asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution and applications to concise stereoselective syntheses of (-)-epi-cytoxazone and the taxotere side-chain

摘要

Dynamic kinetic resolution driven, asymmetric transfer hydrogenation reactions of cyclic sulfamidate imine-5-carboxylate esters were developed. Applications of the new methodology to stereoselective syntheses of the taxotere side-chain and (-)-epi-cytoxazone are described. 1,2-Amino alcohol motifs, including those found in β-amino-α-hydroxy acids, are present in a vast range of natural products and pharmaceutically related compounds. In addition, the relative and absolute stereochemistry of the 1,2-amino alcohol moiety generally governs the biological activities of these substances. Therefore, the development of methods for stereoselective synthesis of members of this family has received considerable attention.