Organocatalytic Enantioselective Stereoablative Hydroxylation of 3‐Halooxindoles: An Effective Method for the Construction of Enantioenriched 3‐Substituted 3‐Hydroxy‐2‐Oxindoles

Abstract

3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).