The Journal of organic chemistry

Enhanced Selectivities for the Hydroxyl-Directed Methanolysis of Esters Using the 2-Acyl-4-aminopyridine Class of Acyl Transfer Catalysts: Ketones as Binding Sites

T Sammakia, TB Hurley

Index: Sammakia, Tarek; Hurley, T. Brian Journal of Organic Chemistry, 2000 , vol. 65, # 4 p. 974 - 978

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Citation Number: 21

Abstract

In this paper we describe the preparation of a series of 2-acyl-4-aminopyridines, and their use as catalysts for the hydroxyl-directed methanolysis of α-hydroxy esters in preference to α- methoxy esters. Hydroxyl-direction with these catalysts, which contain ketones at the 2- position of the pyridine, is achieved by reversible addition of the alcohol of the hydroxy ester to the ketone to provide the corresponding hemiketal. Their activity is compared to that of ...