Chemoenzymatic synthesis of optically active 2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

Abstract

(+/-)-2-Cyano-2-phenyl-1-hexanol 3 was resolved to each enantiomer using Candida rugosa and Pseudomonas fluorescens lipases in 62 and 99% ee, respectively. The absolute stereochemistry of one of the enantiomers was determined to be (S) by diastereomeric amide formation and X-ray crystallography. The resolved alcohols of (R)- and (S)-isomer were transformed to Systhane(R) analogues. (C) 2000 Elsevier Science Ltd. All rights reserved.