Practical Oxirane Ring Opening with In Situ Prepared LiCN; Synthesis of (2S, 3R)-3-(2, 4-Difluorophenyl)-3-hydroxy-2-methyl-4-(1 H-1, 2, 4-triazol-1-yl)-1-butanenitrile

A Tsuruoka, S Negi, M Yanagisawa…

Index: Tsuruoka, Akihiko; Negi, Shigeto; Yanagisawa, Manabu; Nara, Kazumasa; Naito, Toshihiko; Minami, Norio Synthetic Communications, 1997 , vol. 27, # 20 p. 3547 - 3557

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Citation Number: 8

Abstract

Abstract Trisubstituted oxirane 1 was regiospecifically opened with LiCN in situ prepared from acetone cyanohydrin and LiH to provide the corresponding β-hydroxy nitrile 2 in satisfactory yield, enabling us to manufacture a key intermediate for a new antifungal agent on a multi-kg scale. Some applications of this method to the ring opening of other oxiranes and nucleophilic substitution are also described.