Multisubstituted Cyclopentanes by the Domino Michael-Henry
Reaction

doi:10.1055/s-2008-1078148

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Synfacts 2008(10): 1103-1103
DOI: 10.1055/s-2008-1078148

Organo- and Biocatalysis

Multisubstituted Cyclopentanes by the Domino Michael-Henry Reaction

Contributor(s): Benjamin List, Kristina Zumbansen
B. Tan, P. J. Chua, X. Zeng, G. Zhong*
Nanyang Technological University, Singapore

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Publikationsverlauf

Publikationsdatum:
22. September 2008 (online)

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Significance

An organocatalytic and enantioselective domino Michael-Henry reaction yielding highly functionalized chiral cyclopentanes with four stereogenic centers (two quaternary and two tertiary stereocenters) is reported. Using cinchona alkaloid 1 as catalyst a variety of nitroalkanes can be employed in this transformation. Electron-withdrawing as well as electron-donating nitroolefins have a very limited influence on the stereoselectivity. The absolute configuration of the product was determined by X-ray crystallography.