Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids
Yuan Ji, Jessica Sweeney, Jillian Zoglio and David J. Gorin*
*Department of Chemistry, Smith College, Northampton, Massachusetts 01063, Email: dgorinsmith.edu
Y. Ji, J. Sweeney, J. Zoglio, D. J. Gorin, J. Org. Chem., 2013, 78, 11606-11611.
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Dimethylcarbonate is a nontoxic and green methylating reagent. A base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids offers high selectivity for esterification and mild reaction conditions, that enable conservation of stereochemistry at epimerizable stereocenters. Isotope-labeling studies suggest a mechanism via direct methyl transfer from dimethylcarbonate to the substrate.
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C. E. Jacobson, N. Martinez-Muņoz, D. J. Gorin, J. Org. Chem., 2015, 80, 7305-7310.