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Synfacts 2008(9): 0985-0985  
DOI: 10.1055/s-2008-1078670
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Combining Two Organocatalysts in One

Contributor(s): Benjamin List, Lars Ratjen
J. R. Chen, X.-L. An, X.-Y. Zhu, X.-F. Wang, W.-J. Xiao*
Central China Normal University, Hubei, P. R. of China
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Publikationsdatum:
22. August 2008 (online)

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Significance

The coupling of two privileged organocatalyst motifs, proline and cinchonidine, providing catalyst 1 is reported. This multifunctional molecule proved to be effective for the direct aldol reaction between various aromatic aldehydes 2 and acyclic ketones. Acetic acid was found to be the most beneficial additive, assumed to interact with the tertiary amine of the cinchonidine moiety. The reported procedure was not only successful with acetone (3) as nucleophile, also the diastereoselective and enantioselective transformation of aldehydes 2 with 2-butanone (4) was accomplished.