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Copper-Catalyzed Asymmetric [4+1] Cycloadditions of Enones with Diazo Compounds To Form Dihydrofurans

Sunghee Son and Gregory C. Fu*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: gcfmit.edu

S. Son, G. C. Fu, J. Am. Chem. Soc., 2007, 129, 1046-1047.

DOI: 10.1021/ja068344y (free Supporting Information)


Abstract

A planar-chiral bipyridine ligand enables diastereo- and enantioselective copper-catalyzed [4+1] cycloadditions of enones with diazo compounds to produce highly substituted 2,3-dihydrofurans. The method is applied to a catalytic asymmetric synthesis of a deoxy-C-nucleoside.

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Key Words

2,3-dihydrofurans


ID: J48-Y2007-0310