Cinchona-derived thiourea catalyzed hydrophosphonylation of ketimines-an enantioselective synthesis of α-amino phosphonates

A highly enantioselective addition of diphenyl phosphite to ketimines derived from isatins has been developed employing bifunctional thiourea-tertiary amine organocatalysts. A variety of isatins derived ketimines react well with diphenyl phosphite in the presence of Cinchona-derived thiourea (epiCDT) to provide biologically important chiral 3-substituted 3-amino-2-oxindoles (3a-l) in good yield (up to 88%) and good enantioselectivity (up to 97% ee). The three-component version of the reaction through a domino aza-Wittig/phospha-Mannich sequence has successfully been explored.