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Predictably Selective (sp(3))C-O Bond Formation through Copper Catalyzed Dehydrogenative Coupling: Facile Synthesis of Dihydro-oxazinone Derivatives

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Title Predictably Selective (sp(3))C-O Bond Formation through Copper Catalyzed Dehydrogenative Coupling: Facile Synthesis of Dihydro-oxazinone Derivatives
 
Creator MODAK, A
DUTTA, U
KANCHERLA, R
MAITY, S
BHADRA, M
MOBIN, SM
MAITI, D
 
Subject SP(3) C-H
OXIDATIVE MANNICH REACTION
TERTIARY-AMINES
NITROGEN ATOM
MOLECULAR-OXYGEN
TERMINAL ALKYNES
ACTIVATION
TETRAHYDROISOQUINOLINES
FUNCTIONALIZATION
ADJACENT
 
Description An intramolecular dehydrogenative (sp(3))C-O bond formation in salicylamides can be initiated by an active Cu/O-2 species to generate pharamaceutically relevant dihydro-oxazinones. Experimental findings suggest that stereoelectronic parameters in both coupling partners are controlling factors for site selectivity in bond formation. Mechanistic investigations including isotope labeling, kinetic studies helped to propose a catalytic cycle. The method provides a convenient synthesis of an investigational new medicine CX-614, which has potential in finding treatment for Parkinson's and Alzheimer's diseases.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-28T12:53:22Z
2014-12-28T12:53:22Z
2014
 
Type Article
 
Identifier ORGANIC LETTERS, 16(10)2602-2605
1523-7060
1523-7052
http://dx.doi.org/10.1021/ol500670h
http://dspace.library.iitb.ac.in/jspui/handle/100/16616
 
Language English