Selective Esterifications of Primary Alcohols in a Water-Containing Solvent
Yong Wang, Bilal A. Aleiwi, Qinghui Wang and Michio Kurosu*
*Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee Health Science Center, 881 Madison, Memphis, Tennessee 38163-0001, United States, Email: mkurosuuthsc.edu
Y. Wang, B. A. Aleiwi, Q. Wang, M. Kurosu, Org. Lett., 2012, 14, 4910-4913.
DOI: 10.1021/ol3022337 (free Supporting Information)
An oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate, displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3 in 5% H2O-CH3CN. The Oxyma derivative can be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
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Q. Wang, Y. Wang, M. Kurosu, Org. Lett., 2012, 14, 3372-3375.