Tetrahedron letters

Pd-catalyzed aminations of aryl triazolones: effective synthesis of hydroxyitraconazole enantiomers

GJ Tanoury, CH Senanayake, R Hett, AM Kuhn…

Index: Tanoury, Gerald J.; Senanayake, Chris H.; Hett, Robert; Kuhn, Amy M.; Kessler, Donald W.; Wald, Stephen A. Tetrahedron Letters, 1998 , vol. 39, # 38 p. 6845 - 6848

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Citation Number: 48

Abstract

A palladium-catalyzed amination of triazolone 3 by piperazine 2 was used as the key step in an efficient synthesis of highly enantiomerically-pure hydroxyitraconazole isomers. Compound 2 (> 99% ee) was prepared by reaction of an achiral phenol precursor with the corresponding dioxolyl tosylate (> 99% ee), and 3 was made by alkylation of 6 with 7 (> 99% ee).