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: gcf
mit.edu
J. E. Wilson, G. C. Fu, Angew. Chem. Int. Ed., 2006, 45, 1426-1429.
DOI: 10.1002/anie.200503312 (free Supporting Information)
Abstract
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.
see article for more examples
see article for more reactions
Mechanism of nucleophilic catalysis (see C. Zhang, X. Lu, J.
Org. Chem., 1995, 2906.)
Key Words
asymmetric synthesis, homogeneous catalysis, phosphanes, 1,3-dipolar cycloaddition, organocatalysis, cyclopentenes, unsaturated compounds
ID: J06-Y2006-460
