Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2008(10): 1103-1103
DOI: 10.1055/s-2008-1078148
DOI: 10.1055/s-2008-1078148
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Multisubstituted Cyclopentanes by the Domino Michael-Henry Reaction
B. Tan, P. J. Chua, X. Zeng, G. Zhong*
Nanyang Technological University, Singapore
Further Information
Publication History
Publication Date:
22 September 2008 (online)
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.