Enantioselective and Solvent-Controlled Diastereoselective Mannich Reaction of Isatin Imines with Hydroxyacetone: Synthesis of 3-Substituted 3-Aminooxindoles

Abstract

The diastereoselectively switchable enantioselective Mannich reaction of isatin imines with hydroxyacetone is reported. The chiral primary amino acid catalyzed this Mannich reaction to afford both anti- and syn-Mannich adducts in high yields, good diastereoselectivities, and enantioselectivities. The reason for the solvent control of the diastereoselectivity phenomenon was investigated.