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Synfacts 2010(4): 0433-0433  
DOI: 10.1055/s-0029-1219469
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Asymmetric C-H Insertion of α-Diazosulfones

Contributor(s): Mark Lautens, Chit Tsui
C. J. Flynn, C. J. Elcoate, S. E. Lawrence, A. R. Maguire*
University College Cork, Ireland
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

α-Diazocarbonyl compounds have been successfully employed in synthetically powerful C-H insertion processes. Compared to the success of rhodium-catalyzed enantioselective C-H insertions with α-diazocarbonyl compounds, the application of copper catalysts to such transformations has been very limited to date. Only modest enantioselectivities have been reported (up to 60% ee in intramolecular and 88% ee in ­intermolecular cases). The authors reported that by using copper bisoxazoline 1 catalysts. The C-H insertion of α-diazosulfones can lead to enantioenriched cyclic sulfones (thiopyrans or sulfolanes) with up to 98% ee.