Stereoselective Synthesis of 1,2,3-Triazolooxazine and Fused 1,2,3-Triazolo-delta-Lactone Derivatives

Gümüş A., Mert K., TANYELİ C.

HELVETICA CHIMICA ACTA, vol.97, no.10, pp.1340-1344, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 97 Issue: 10
  • Publication Date: 2014
  • Doi Number: 10.1002/hlca.201300441
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1340-1344
  • Keywords: 1, 2, 3-Triazolooxazine, 1, 2, 3-Triazolo--lactone, Cyclohexanol, 2-azido-, Azidealkyne cycloaddition, Cycloadditions, Enzymatic resolution, WALLED CARBON NANOTUBES, CLICK-CHEMISTRY
  • Middle East Technical University Affiliated: Yes

Abstract

The stereoselective synthesis of 1,2,3-triazolooxazine and fused 1,2,3-triazolo--lactone by applying chemoenzymatic methods is described. trans-2-Azidocyclohexanol was successfully resolved by Novozyme 435 with an ee value of 99%. Installation of the alkyne moiety on the enantiomerically enriched azidoalcohol by O-alkylation, followed by intramolecular azidealkyne [3+2] cycloaddition resulted in the desired 1,2,3-triazolooxazine derivative. Enantiomerically pure azidocyclohexanol was also subjected to the Huisgen 1,3-dipolar cycloaddition reaction with dimethylacetylene dicarboxylate, followed by intramolecular cyclization of the corresponding cycloadduct, to furnish a fused 1,2,3-triazolo--lactone.