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Synfacts 2006(7): 0689-0689  
DOI: 10.1055/s-2006-941867
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective α-Oxygenation ofα-Diazoesters

Contributor(s): Mark Lautens, Andrew Martins
T. C. Maier, G. C. Fu*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

In the presence of a Cu(II)/bisazaferrocene ligand, a variety of α-diazoesters were converted into the corresponding α-ether with unprecedented levels of enantioselectivity. Yields and ee values vary from moderate to excellent, and a variety of α-diazoesters and alcohols were used. The reaction is proposed to occur via an enantio­selective carbenoid O-H insertion reaction.