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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.

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.

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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