A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates

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 functionali...

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Bibliographic Details
Published in:Organic letters 2007-12, Vol.9 (25), p.5327-5329
Main Authors: Mueller, Amanda J, Jennings, Michael P
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702546w