Conformationally restricted 4-dimethylaminopyridine (DMAP) analogs: synthesis and evaluation of catalytic effectiveness |
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Authors: | Satwinder Singh |
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Affiliation: | Department of Chemistry, University of Texas at San Antonio, San Antonio, TX 78249-0698, USA |
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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. |
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Keywords: | Nucleophilic catalysis Acylation of alcohols 4-Dimethylaminopyridine Sonogashira reaction Cyclization |
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