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

Add time:07/11/2019    Source:sciencedirect.com

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.

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