Enantioselective alkynylation of benzo[e][1,2,3]-oxathiazine 2,2-dioxides catalysed by (R)-VAPOL-Zn complexes: synthesis of chiral propargylic cyclic sulfamidates

Org Biomol Chem. 2015 Jul 21;13(27):7393-6. doi: 10.1039/c5ob01012h.

Abstract

(R)-VAPOL-Zn(II) complexes catalysed the enantioselective addition of terminal alkynes to cyclic benzoxathiazine 2,2-dioxides, providing the corresponding chiral propargylic sulfamidates with high yields (up to 93%) and good enantiomeric excesses (up to 87%).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Crystallography, X-Ray
  • Ligands
  • Pargyline / analogs & derivatives*
  • Pargyline / chemical synthesis
  • Pargyline / chemistry
  • Phenanthrenes / chemistry*
  • Propanols
  • Propylamines / chemical synthesis*
  • Propylamines / chemistry
  • Stereoisomerism
  • Thiazines / chemistry*
  • Zinc / chemistry*

Substances

  • Alkynes
  • Amides
  • Ligands
  • Phenanthrenes
  • Propanols
  • Propylamines
  • Thiazines
  • VAPOL ligand
  • propargylamine
  • Pargyline
  • Zinc