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A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates

Amanda J. Mueller and Michael P. Jennings*

*Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, Email: jenningmbama.ua.edu

A. J. Mueller, M. P. Jennings, Org. Lett., 2007, 9, 5327-5329.

DOI: 10.1021/ol702546w (free Supporting Information)


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Abstract

In the TMSOTf-mediated catalytic carbocupration of ynoates, catalyst loadings as low as 5 mol % readily allow for high yields and diastereoselectivities for a series of aromatic Grignard reagents. A vicinally functionalization is possible via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.

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ID: J54-Y2007-4060