Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 19, Pages 7775-7778Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo801337k
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Funding
- DST [SR/S1/OC-22/2006]
- CSIR
- UGC, India
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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.
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