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Synfacts 2008(3): 0312-0312  
DOI: 10.1055/s-2008-1042723
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Tandem Oxidative Dearomatization-Michael Reaction

Contributor(s): Benjamin List, Subhas Chandra Pan
N. T. Vo, R. D. M. Pace, F. O’Hara, M. J. Gaunt*
University of Cambridge, UK
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Publikationsverlauf

Publikationsdatum:
21. Februar 2008 (online)

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Significance

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.