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Synfacts 2007(5): 0508-0508  
DOI: 10.1055/s-2007-968452
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed [4+1] Cycloadditions of Enones with Diazo Compounds

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Son, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

This paper describes the enantio­selective synthesis of 2,3-dihydrofurans through a copper-catalyzed [4+1] cycloaddition of enones and diazo compounds. The use of bpy* (1) as chiral ligand gave the best results when compared to a variety of other ligands including bis(oxazolines), semicorrin and others. Enones containing unsaturated substituents (i.e., aryl and heteroaryl) provided high ee values (87-93% ee), while alkyl-substituted enones gave only modest selectivities (71-78% ee).