Organocatalytic Stereodivergent Dearomatization and N-Acylation of 2-Amino-3-subsituted Indoles

Abstract

Organocatalytic chemo- and enantioselective reactions of 2-amino-3-subsituted indoles have been achieved for the first time. Via asymmetric allylic alkylation of Morita-Baylis-Hillman carbonates, organocatalytic enantioselective dearomatization of 2-amino-3-subsituted indoles afforded an array of enantioenriched 3,3-disubstituted indolin-2-imines bearing a quaternary carbon stereocenter in 34-79% yields with 61-91% ee. With Boc₂O as reaction partner, the organocatalytic enantioselective N-acylation of 2-amino-3-subsituted indoles was established to furnish C-N axially chiral products in 22-98% yields with 73-92% ee.