Enantioselective Aminative Dearomatization of Indoles via Electrophilic 1,6-Addition of <i>p</i>-Quinone Diimides (<i>p</i>-QDIs)
Parbat Subba, Sushree Ranjan Sahoo, Chhavi Khajuria, Vinod K. Singh
Abstract
Herein we report the first use of p -quinone diimide for the aminative dearomatization of 2,3-disubstituted indoles to furnish C3 aza-quaternary chiral indolenines. This approach, which proceeds via an electrophilic 1,6-addition of p -quinone diimide, allows the synthesis of an array of optically active aza-quaternary indolenines with high yields and excellent enantioselectivities. A one-pot approach of the same has also been established to further improve the synthetic accessibility of this protocol.
Topics & Concepts
ChemistryElectrophileEnantioselective synthesisQuinoneDiimideCombinatorial chemistryTotal synthesisStereochemistryOrganic chemistryMoleculeCatalysisPeryleneCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis