Journal
TETRAHEDRON LETTERS
Volume 48, Issue 11, Pages 1983-1986Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.01.066
Keywords
nucleophilic catalysis; acylation of alcohols; 4-dimethyl-aminopyridine; sonogashira reaction; cyclization
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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. (c) 2007 Elsevier Ltd. All rights reserved.
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