Synthesis of Functionalized Cyclopentenes through Catalytic Asymmetric [3+2] Cycloadditions of Allenes with Enones
Jonathan E. Wilson, Gregory C. Fu*
*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA, Email: gcfmit.edu
J. E. Wilson, G. C. Fu, Angew. Chem. Int. Ed., 2006, 45, 1426-1429.
A nucleophile-catalyzed asymmetric [3+2] cycloaddition of allenes with enones is described. The method has also been applied to reactions of trisubstituted olefins, thereby generating quartenary and tertiary stereocenters.
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Mechanism of nucleophilic catalysis (see C. Zhang, X. Lu, J. Org. Chem., 1995, 2906.)