Catalytic asymmetric synthesis of γ-substituted vinyl sulfones.
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.
Department of Organic Chemistry I, Universidad del País Vasco, Apdo. 1072, Manuel de Lardizabal 3, 20018 San Sebastián, Spain.
Rosa
R
López
Maitane
M
Zalacain
Claudio
C
Palomo
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D009574:Nitro Compounds; D013450:Sulfones; D014753:Vinyl Compounds