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A New Oxyma Derivative for Nonracemizable Amide-Forming Reactions in Water

Qinghui Wang, Yong 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

Q. Wang, Y. Wang, M. Kurosu, Org. Lett., 2012, 14, 3372-3375.

DOI: 10.1021/ol3013556 (free Supporting Information)


Abstract

In the presence of the Oxyma derivative 2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate, short peptides to oligopeptides could be synthesized by using EDCI and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.

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Selective Esterifications of Primary Alcohols in a Water-Containing Solvent

Y. Wang, B. A. Aleiwi, Q. Wang, M. Kurosu, Org. Lett., 2012, 14, 4910-4913.


Key Words

Amides


ID: J54-Y2012-2220