Synthesis

N-Acylpyridinium Trifluoromethanesulfonates and Tetrafluoroborates: Shuttle Reagents for the Acylation of Enantiopure Secondary Alcohols

R Wagner, W Günther, E Anders

Index: Wagner, Ruediger; Guenther, Wolfgang; Anders, Ernst Synthesis, 1998 ,  # 6  p. 883 - 888

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Citation Number: 5

Abstract

Abstract: Several enantiopure alcohols are esterified with N-acyl-4-benzylpyridinium trifluoromethanesulfonates 7b, d, f or tetrafluoroborates 7a, c, e. These reagents, which can be generated in situ, or isolated as stable salts, are synthesized from readily available 4- alkylpyridines 3, acyl chlorides 4 and strong protic acids 6. The acyl moiety is transferred under neutral conditions and in high yields. The heterocyclic component 3a can be re- ...