Elsevier

Tetrahedron

Volume 56, Issue 10, 3 March 2000, Pages 1309-1314
Tetrahedron

Chemoenzymatic Synthesis of Optically Active 2-Phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile

https://doi.org/10.1016/S0040-4020(00)00031-4Get rights and content

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® analogues.

Section snippets

General

1H NMR (250 or 300 MHz) and 13C NMR spectra (63 or 75 MHz) were recorded on a Varian Gemini 250 or 300 MHz spectrometer with TMS as an internal reference. IR spectra were recorded on a MIDAC 101025 FT-IR spectrometer and optical rotation was measured on Autopol® III polarimeter (Rudolph Research Co.). Low EI resolution mass spectra were determined on HP GC 5972 [Column: Hewlett-Packard fused silica capillary column HP-5 cross-linked 5% Phenyl methyl silicone, Column ID 0.20 mm, Film thickness: 0.11 

Acknowledgements

We are grateful to the Korea Institute of Science and Technology for financial support and Dr Kwan Mook Kim for X-ray crystallographic analysis.

References (9)

  • W Kramer et al.

    Pesticide Chemistry

    Human Welfare and the Environment

    (1983)
  • G Haug et al.
  • B.C Baldwin et al.

    Pestic. Sci.

    (1984)
  • (a) Brieva, R.; Crich, J. Z.; Sih, C. J. J. Org. Chem. 1993, 58, 1068. (b) Hallinan, K. O.; Honda, T. Tetrahedron 1995,...
There are more references available in the full text version of this article.

Cited by (0)

View full text