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Synfacts 2009(12): 1402-1402  
DOI: 10.1055/s-0029-1218216
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Bicyclic Prolinol Silyl Ether Catalysts

Contributor(s): Benjamin List, Saihu Liao
R.-S. Luo, J. Weng, H.-B. Ai, G. Lu*, A. S. C. Chan
Sun Yat-sen University, Guangzhou and The Hong Kong Polytechnic University, Kowloon, P. R. of China
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Publikationsdatum:
20. November 2009 (online)

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Significance

Several bicyclic prolinol derivatives were prepared and evaluated as catalysts for the Michael addition of aldehydes to nitroolefins. The novel bicyclic perhydroindolinol silyl ether 1 showed excellent stereocontrol in this transformation providing the corresponding adducts in nearly optically pure form (er up to 99.5:0.5) and with high diastereoselecitivity (syn/anti up to 99:1).