Stereocontrolled Creation of Adjacent Quaternary and Tertiary Stereocenters by a Catalytic Conjugate Addition


  • This work was supported financially by the National Institutes of Health (GM-61591) and by a Sloan Research Fellowship (L.D.).


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Not too close for comfort: Practical chiral organocatalysts like that shown promote Michael addition reactions of a wide range of trisubstituted carbon nucleophiles to various nitroalkenes, often with nearly perfect stereoselectivity (>99 % ee and >98:2 d.r.). In one step adjacent carbon- or heteroatom-substituted quaternary and tertiary stereocenters are generated from readily available starting materials.