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Synfacts 2009(12): 1367-1367  
DOI: 10.1055/s-0029-1218314
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Kinetic Resolution of Pyrazolidinones by a Cu(II)-Catalyzed Diels-Alder Reaction

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
M. P. Sibi*, K. Kawashima, L. M. Stanley
North Dakota State University, Fargo, USA
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Publication History

Publication Date:
20 November 2009 (online)

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Significance

The authors have developed a ­Diels-Alder (DA) cycloaddition strategy for the kinetic resolution of chiral pyrazolidinones. The desired pyrazolidinones were obtained in good yields and excellent enantioselectivities after removal of amide bonds with little erosion of the enantiomeric excess. It is interesting that this strategy utilized a relay of stereochemical information from a permanent chiral center to a fluxional chiral center at the nitrogen center.