Predictably selective (sp3)C-O bond formation through copper catalyzed dehydrogenative coupling: facile synthesis of dihydro-oxazinone derivatives.
An intramolecular dehydrogenative (sp(3))C-O bond formation in salicylamides can be initiated by an active Cu/O2 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.
Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, India.
Atanu
A
Modak
Uttam
U
Dutta
Rajesh
R
Kancherla
Soham
S
Maity
Mohitosh
M
Bhadra
Shaikh M
SM
Mobin
Debabrata
D
Maiti