title: Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide-alkene cycloaddition on D-ribose derived nitriles: an efficient synthetic route to isoxazoline fused five and six membered carbocycles.
abstract: An efficient synthetic route to isoxazoline fused carbocycles from carbohydrate scaffolds that comprise of free hydroxyl group(s) is described with high regio- and stereoselectivity. Montmorillonite K-10/chloramine T oxidation and in situ intramolecular nitrile oxide-alkene cycloaddition (INOC) of D-ribose derived oximes have been developed for the diversity oriented synthesis of isoxazoline fused five and six membered carbocycles.
authors.affiliation: School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar, Orissa 751007, India.
authors.forename: Amarendra
authors.initials: A
authors.lastname: Panda
authors.affiliation: School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar, Orissa 751007, India.
authors.forename: Sulagna
authors.initials: S
authors.lastname: Das
authors.affiliation: School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Bhubaneswar, Orissa 751007, India. Electronic address: spal@iitbbs.ac.in.
authors.forename: Shantanu
authors.initials: S
authors.lastname: Pal
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000538:Aluminum Silicates / Q000737:chemistry*; D000077215:Clay; D061565:Cycloaddition Reaction; D006863:Hydrogen-Ion Concentration; D007555:Isoxazoles / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D012266:Ribose / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000475:Alkenes; D000538:Aluminum Silicates; D007555:Isoxazoles; D009570:Nitriles; D010087:Oxides; D012266:Ribose; D000077215:Clay
keywords: Chloramin-T; Dipolar cycloadditions; Isoxazoline fused carbocycles; Montmorillonite K-10; Nitrile oxides; d-Ribose