Tetrahedron letters

Conformationally restricted 4-dimethylaminopyridine (DMAP) analogs: synthesis and evaluation of catalytic effectiveness

S Singh, G Das, OV Singh, H Han

Index: Singh, Satwinder; Das, Goutam; Singh, Om V.; Han, Hyunsoo Tetrahedron Letters, 2007 , vol. 48, # 11 p. 1983 - 1986

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Citation Number: 26

Abstract

The syntheses of a series of conformationally restricted 4-dimethylaminopyridine (DMAP) analogs 1–3 are described. Evaluations of catalyst effectiveness demonstrated that 1 was the best catalyst for the acetylation reaction of a tertiary alcohol, while 2 and 3 were roughly comparable to DMAP. The order of effectiveness of these catalysts roughly parallels their acetylation enthalpies estimated from ab initio calculations.