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

Published as part of the Special Topic Modern Strategies with Iodine in Synthesis

Abstract

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.

Key words

catalysis - chirality - dearomatization - hydroxylation - hypervalent iodine - oxidation

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