Asymmetric Synthesis of Chiral Aldehydes by Conjugate Additions with Bifunctional Organocatalysis by Cinchona Alkaloids


  • This work was supported financially by the National Institutes of Health (GM-61591). We thank Stephen C. Wilson for his contribution to the studies described herein.


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A highly efficient asymmetric conjugate addition of carbonyl donors to α,β-unsaturated aldehydes is realized with 6′-OH cinchona alkaloids as bifunctional organocatalysts. A wide range of α-substituted β-ketoesters and α-substituted α-cyanoacetates can be employed as donors, whereas acrolein and β-substituted α,β-unsaturated aldehydes are suitable acceptors for this enantioselective addition.