Silyl Cation-Initiated, Brønsted Acid-Catalyzed Strategy toward Unsymmetrical 3,3-Disubstituted 2-Oxindoles and Azonazine Cores
Jabir Khan, Naveen Yadav, Aparna Tyagi, Chinmoy Kumar Hazra
Abstract
Herein, a mild, metal-free, robust approach for synthesizing valuable and sterically demanding unsymmetrical 3,3-disubstituted 2-oxindoles via reductive cyclization of α-ketoamides is reported. This operationally simple protocol is initiated by a silyl cation and further catalyzed by a Brønsted acid. We have utilized a wide range of arenes, amines, and thiols as coupling partners with various α-ketoamides. The products were afforded in excellent regioselectivity and good functional group tolerance. This procedure provides easy access to the scaffolds of azonazine and its derivatives with an excellent syn-diastereoselectivity bearing all-carbon quaternary stereocenters.
Topics & Concepts
ChemistryStereocenterRegioselectivitySilylationSteric effectsCatalysisBrønsted–Lowry acid–base theoryCombinatorial chemistryFunctional groupOrganic chemistryEnantioselective synthesisPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsChemical Synthesis and Analysis