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A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates

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journal contribution
posted on 06.12.2007, 00:00 by Amanda J. Mueller, Michael P. Jennings
The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereoselectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.