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Catalytic asymmetric synthesis of γ-substituted vinyl sulfones
Rosa López1, Maitane Zalacain, Claudio Palomo
1Department of Organic Chemistry I, Universidad del País Vasco, Apdo. 1072, Manuel de Lardizabal 3, 20018 San Sebastián, Spain.
Abstract:
A fast new entry for the stereoselective construction of γ-substituted vinyl sulfones is presented. The key for success is the use of a readily available chiral secondary amine catalyst that allows the use of base-sensitive β-nitroethyl sulfones as masked β-sulfonyl vinyl anions in conjugate additions. The method performed in a three-step one-pot operation gives access to a great variety of vinyl sulfones in good yields and with excellent enantioselectivities. The method has also been extended to other relatively base-sensitive β-electron-withdrawing-substituted nitroalkanes to afford products with manifold functionality, providing a quick entry to very attractive synthetic intermediates for organic synthesis.
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