Transition-state stabilization via dynamic molecular recognition : a concerted acid-base bifunctional catalysis in ester hydrolysis

doi:10.1016/S0040-4039(00)92300-1

Tetrahedron Letters

Volume 32, Issue 36, 1991, Pages 4757-4760

https://doi.org/10.1016/S0040-4039(00)92300-1 Get rights and content

Abstract

An imidazole derivative 1a having a bisresorcinol moiety catalyzes the hydrolysis of p-nitrophenyl acetate in H₂O-CH₃CN (9:1) by the mechanism involving a concerted acid-base cooperation; nucleophilic attack of the imidazolyl group on substrate is assisted by the hydroxyl group of the bisresorcinol moiety as a general acid.

The hydrolysis of p -nitrophenyl acetate is accelerated by a bifunctional catalyst containing imidazole and bisresorcinol moieties.

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^☆: Molecular Recognition. 17. Part 16: Aoyama, Y.; Asakawa, M.; Matsui, Y.; Ogoshi, H. J. Am. Chem. Soc., in press.

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Transition-state stabilization via dynamic molecular recognition : a concerted acid-base bifunctional catalysis in ester hydrolysis☆

Abstract

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.