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Organocatalytic Tandem Oxidative Dearomatization-Michael Reaction
N. T. Vo, R. D. M. Pace, F. O’Hara, M. J. Gaunt*
University of Cambridge, UK
21 February 2008 (online)
The authors report an enantioselective organocatalytic tandem oxidative dearomatization-Michael reaction. Diacetoxyiodobenzene was used as oxidant and catalyst 1 was found to be the best catalyst for the desymmetrizing Michael reaction. The authors found that methanol can act both as nucleophile and as solvent for this tandem operation. With 10 mol% of catalyst 1, good to high diastereoselectivities (dr = 6.7:1 to >20:1 dr) and excellent enantioselectivities (er = 98:2 to >99:1) are obtained for different phenols. Lower enantioselectivity (er = 70:30) was obtained when a substituted 2,6-dimethyl phenol was used.