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Vicinal Functionalization of Propiolate Esters via Catalytic Carbocupration: Stereoselective Formation of Substituted Vinyl Silanes

Amanda J. Mueller Hendrix and Michael P. Jennings*

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

A. J. Mueller Hendrix, M. P. Jennings, Org. Lett., 2010, 12, 2750-2753.

DOI: 10.1021/ol100854j (free Supporting Information)


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Abstract

A copper-catalzed functionalization of propiolate esters with various Grignard reagents in presence of trimethylsilyl trifluoromethanesulfonate enables the synthesis of substituted E-vinyl silanes in good yields and excellent diastereoselectivities via a catalytic carbocupration-silicon group migration sequence.

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Key Words

vinylsilanes, unsaturated compounds


ID: J54-Y2010-1640