Tetrahedron letters

Thermodynamic and kinetic considerations in the chemoselective O-acylation by mixed anhydrides. A semiempirical MO approach

AJ Mota, R Robles, LA de Cienfuegos, A Lamenca

Index: Mota, Antonio J.; Robles, Rafael; De Cienfuegos, Luis Alvarez; Lamenca, Alberto Tetrahedron Letters, 2004 , vol. 45, # 17 p. 3349 - 3353

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Citation Number: 2

Abstract

A simple methodology to achieve high chemoselective O-acylation of primary hydroxy groups, in the presence of secondary ones, was performed by means of the quick generation of a mixed anhydride using mild and inexpensive conditions. Steric and electronic factors are involved in this preference. As far as the geometries are concerned, semiempirical calculations were carried out in order to determine the nature of the ...