e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521
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
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.
