Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals

JM Wurst, G Liu, DS Tan

Index: Wurst, Jacqueline M.; Liu, Guodong; Tan, Derek S. Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7916 - 7925

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Citation Number: 33

Abstract

Mechanistic investigations of a MeOH-induced kinetic epoxide-opening spirocyclization of glycal epoxides have revealed dramatic, specific roles for simple solvents in hydrogen- bonding catalysis of this reaction to form spiroketal products stereoselectively with inversion of configuration at the anomeric carbon. A series of electronically tuned C1-aryl glycal epoxides was used to study the mechanism of this reaction based on differential reaction ...