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Synfacts 2006(2): 0166-0166  
DOI: 10.1055/s-2005-924801
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

A General Organocatalyst for the Asymmetric Direct α-Functionalization of Aldehydes

Contributor(s): Benjamin List, Daniela Kampen
J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen*
Aarhus University, Denmark
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Publikationsdatum:
23. Januar 2006 (online)

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Significance

A general organocatalyst for asymmetric α-functionalizations of aldehydes has been designed. Chiral α,α-diarylprolinol silyl ether 1 catalyzes Michael and Mannich reactions, as well as α-aminations, α-fluorinations, α-brominations, and α-sulfenylations of aldehydes in good yields and enantioselectivities. The reactions presumably proceed via an enamine intermediate. In addition, mechanistic considerations based on the interpretation of experimental data, kinetic studies, and computational investigations are provided.