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Synfacts 2008(1): 0089-0089
DOI: 10.1055/s-2007-991420
DOI: 10.1055/s-2007-991420
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
Generation of Five Stereocenters in an Organocatalytic Cascade Reaction
E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen*
Aarhus University, Denmark
Further Information
Publication History
Publication Date:
18 December 2007 (online)
Significance
The generation of five stereocenters in one tandem reaction yielding optically active cyclohexanes is reported. In this cascade reaction, an α,β-unsaturated aldehyde is activated towards the Michael addition of a 1,3-bisnitroalkane by a chiral pyrrolidine. After hydrolysis of the intermediate enamine, the reaction sequence is completed by a Henry reaction to give cyclohexanes with good enantioselectivities and relatively high diastereoselectivities.