Enantioselective 4-Hydroxylation of Phenols under Chiral Organoiodine(I/III) Catalysis

A procedure for the intermolecular enantioselective dearomatization of phenols under chiral (I/III) catalysis is reported. This protocol employs 3-chloroperoxybenzoic acid (m-CPBA) as the terminal oxidant together with a defined C-2-symmetric aryl iodide as the effective organocatalyst. This enantioselective reaction proceeds with complete selectivity under mild conditions and enables the hydroxylative dearomatization of a number of phenols to give the corresponding p-quinol products with up to 50% ee.