Direct transacylation of 2, 2, 2-trihaloethyl esters with amines and alcohols using phosphorus (III) reagents for reductive fragmentation and in situ activation
JJ Hans, RW Driver, SD Burke
Index: Hans, Jeremy J.; Driver, Russell W.; Burke, Steven D. Journal of Organic Chemistry, 2000 , vol. 65, # 7 p. 2114 - 2121
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Citation Number: 36
Abstract
Amides and esters have been synthesized from 2, 2, 2-trihaloethyl esters in one pot using phosphorus (III) reagents as reductants, with resultant carboxylate activation as an acyloxyphosphonium intermediate, and in situ trapping by amine or alcohol nucleophiles. Secondary and tertiary amides were synthesized, including a dipeptide, in good yields using hexamethylphosphorous triamide,(Me2N) 3P, as reducing agent. Optimal yields of esters ...
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