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Synfacts 2009(11): 1275-1275  
DOI: 10.1055/s-0029-1218110
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

An Effective Combination of Prolinamides and BINOLs

Contributor(s): Benjamin List, Saihu Liao
Y.-Q. Cheng, Z. Bian, Y.-B. He, F.-S. Han, C.-Q. Kang, Z.-L. Ning, L.-X. Gao*
Changchun Institute of Applied Chemistry, P. R. of China
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

A series of novel l-prolinamide derivatives was prepared and applied to the Michael addition of aldehydes to nitroolefins. The catalyst/co-catalyst combination of (S)-2-(2′-piperidinyl)pyridine-derived trans-4-hydroxy-l-prolin­amide and (S)-BINOL was found to be very efficient. With only 1 mol% of prolinamide catalyst and 1 mol% of (S)-BINOL as co-catalyst, the conjugate addition products can be obtained in high yields and with high diastereo- and enantioselectivity (dr up to 99:1; er up to 99.5:0.5).