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Synfacts 2008(10): 1104-1104  
DOI: 10.1055/s-2008-1078152
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Proline Ionic Liquid in Asymmetric Michael Additions

Contributor(s): Benjamin List, Lars Ratjen
Y. Qian, S. Xiao, L. Liu, Y. Wang*
Nankai University, Tianjin, P. R. of China
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Publication History

Publication Date:
22 September 2008 (online)

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Significance

A mild and efficient method for the asymmetric Michael addition of cyclohexanone to various chalcones is reported. The reusable ionic liquid (IL) [EMIm][Pro] 1 was used as chirality inductor. The products were obtained in moderate to excellent yields and moderate to high enantio­selectivities in the presence of co-solvents like methanol. Interestingly, the enantioselectivity in DMSO as co-solvent was found to be inverted. The reaction can be assumed to proceed via intermediate 2.