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. 2009 Apr 18;65(16):3139-3148.
doi: 10.1016/j.tet.2008.11.054.

Catalytic enantioselective conjugate additions with α,β-unsaturated sulfones

Hongming Li  1 , Jun Song, Li Deng
Affiliations

Catalytic enantioselective conjugate additions with α,β-unsaturated sulfones

Hongming Li et al. Tetrahedron. .

Abstract

We describe the development of a highly efficient catalytic asymmetric conjugate addition to α,β-unsaturated sulfones. Utilizing practical bifunctional organic catalysts and involving air- and moisture-tolerant conditions, conjugate additions of a wide range of Michael donors to α,β-unsaturated sulfones proceeded in excellent enantioselectivity/diastereoselectivity and high yield. This efficient and operationally simple new catalytic asymmetric reaction should provide a versatile approach for the asymmetric synthesis of chiral sulfones bearing all-carbon quaternary stereocenters.

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Figures

Scheme 1
Scheme 1
Rational for the development of a catalytic asymmetric conjugate addition to α, β-unsaturated sulfones (4) with 6'-OH cinchona alkaloids 5
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