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Synfacts 2006(2): 0166-0166
DOI: 10.1055/s-2005-924801
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
J. Franzén, M. Marigo, D. Fielenbach, T. C. Wabnitz, A. Kjærsgaard, K. A. Jørgensen*
Aarhus University, Denmark
Further Information
Publication History
Publication Date:
23 January 2006 (online)
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.