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Synfacts 2006(8): 0841-0841
DOI: 10.1055/s-2006-942023
DOI: 10.1055/s-2006-942023
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Cinchona Alkaloid Catalyzed Asymmetric Synthesis of Chiral Aldehydes
F. Wu, R. Hong, J. Khan, X. Liu, L. Deng*
Brandeis University, Waltham, USA
Further Information
Publication History
Publication Date:
21 July 2006 (online)
![](https://www.thieme-connect.de/media/synfacts/200608/lookinside/thumbnails/10.1055-s-2006-942023-1.jpg)
Significance
The authors developed a highly efficient and versatile 6′-OH cinchona alkaloid catalyzed conjugate addition of carbonyl donors to α,β-unsaturated aldehydes to synthesize chiral aldehydes with excellent yields and enantioselectivities. A wide range of carbonyl donors (α-substituted-β-keto esters in the presence of bifunctional organocatalyst A or α-cyano esters in the presence of B) and α,β-unsaturated aldehydes can be used to form tetrasubstituted stereocenters. This new methodology was successfully applied to the catalytic enantioselective total synthesis of (+)-tanikolide.