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Synfacts 2006(5): 0499-0499  
DOI: 10.1055/s-2006-934449
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Catalytic Asymmetric Tandem Conjugate Addition-Protonation Reaction

Contributor(s): Benjamin List, Sebastian Hoffmann
Y. Wang, X. Liu, L. Deng*
Brandeis University, Massachusetts, USA
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Publikationsdatum:
21. April 2006 (online)

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Significance

This paper describes the asymmetric tandem conjugate addition-protonation reaction of various α-cyano ketones, α-cyano esters and β-keto esters with 2-chloroacrylnitril using 6′-hydroxy cinchona alkaloids as dual function catalysts. The desired products, which contain 1,3-tertiary-quaternary stereocenters, were obtained in moderate to good diastereoselectivities and excellent enantioselectivities (12 cyclic and acyclic examples, up to 25:1 dr, up to 99% ee).