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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Predictably selective (sp3)C-O bond formation through copper catalyzed dehydrogenative coupling: facile synthesis of
Atanu Modak1, Uttam Dutta, Rajesh Kancherla
1Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, India.
Abstract:
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.
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