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.
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.
Chatterjee
Nirbhik
N
Department of Chemistry, University Colleges of Science and Technology, University of Calcutta, 92, A. P. C. Road, Kolkata-700009, India.
Pandit
Palash
P
Halder
Samiran
S
Patra
Amarendra
A
Maiti
Dilip K
DK