title: Generation of nitrile oxides under nanometer micelles built in neutral aqueous media: synthesis of novel glycal-based chiral synthons and optically pure 2,8-dioxabicyclo[4.4.0]decene core.
abstract: A highly efficient strategy for chemoselective oxidation of aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media is reported. Their in situ intermolecular 1,3-dipolar cycloaddition (1,3-DC) with olefins in nanometer aqueous micelles occurs with improved stereoselectivity and acceleration of reaction rate toward synthesis of new chiral synthons, 3-(2'-C-3',4',6'-tri-O-benzylglycal)-Delta(2)-isoxazolines and others. Construction of optically pure 2,8-dioxabicyclo[4.4.0]decene skeleta is performed by this green approach, and the stereochemistry of the new chiral center is predicted by B3LYP density functional theory.
authors.affiliation: Department of Chemistry, University Colleges of Science and Technology, University of Calcutta, 92, A. P. C. Road, Kolkata-700009, India.
authors.forename: Nirbhik
authors.initials: N
authors.lastname: Chatterjee
authors.forename: Palash
authors.initials: P
authors.lastname: Pandit
authors.forename: Samiran
authors.initials: S
authors.lastname: Halder
authors.forename: Amarendra
authors.initials: A
authors.lastname: Patra
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Maiti