Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: An effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles

Article abstract of DOI:10.1002/chem.201201395

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).