title: Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides.
abstract: The TMSOTf-mediated synthesis of β-configured spirocyclic 2-substituted-2-oxazoline ribosides was achieved using a "Ritter-like" reaction in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-β-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived spirooxazolines are stable and were obtained in good yield with high stereoselectivity due to the conformational rigidity imparted by the 3,4-isopropylidene group.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Pune 411 008, India.
authors.forename: Madhuri
authors.initials: M
authors.lastname: Vangala
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research, Pune 411 008, India.
authors.forename: Ganesh P
authors.initials: GP
authors.lastname: Shinde
keywords: Ritter reaction; fructose; oxazoline; riboside; spiro