Ulose formation by selenoxide elimination

  title={Ulose formation by selenoxide elimination},
  author={Christine E. Heath and Maria C. Gillam and Carrie S. Callis and Robert R. Patto and Christopher J. Abelt},
Abstract Ring opening of methyl 2,3-anhydro-( R )-4,6- O -benzylidene- α - d -mannopyranoside with phenyl selenide gives ( R )-4,6- O -benzylidene-3- Se -phenyl-3-seleno- α - d -altropyranoside ( 2 ). Oxidation of ( 2 ) with H 2 O 2 followed by thermolysis gives methyl ( R )-4,6- O -benzylidene-3-deoxy- α - d - erythro -hexopyranosid-2-ulose via syn -elimination and ketoenol tautomerization.