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Modified Shapiro Reactions with Bismesitylmagnesium As an Efficient Base Reagent

William J. Kerr*, Angus J. Morrison, Marek Pazicky and Tina Weber

*Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland, U.K., Email: w.kerrstrath.ac.uk

W. J. Kerr, A. J. Morrison, M. Pazicky, T. Weber, Org. Lett., 2012, 14, 2250-2253.

DOI: 10.1021/ol300652k (free Supporting Information)


Abstract

After treatment with bismesitylmagnesium, a range of tosylhydrazones furnishes exceptionally high incorporation of the introduced electrophiles and good yields of the functionalized styrenes. At conveniently accessible temperatures and with a comparably small excess of base reagent and electrophile (for example 1.05 equiv of Weinreb amides), this modified Shapiro reaction offers an efficient alternative to the lithium-mediated process.

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Key Words

Shapiro Reaction, Weinreb Ketone Synthesis, Enones


ID: J54-Y2012-1310