ChemInform Abstract: Organocatalytic Synthesis of α‐Quaternary Amino Acid Derivatives via Aza‐Friedel—Crafts Alkylation of Indoles with Simple α‐Amidoacrylates.

Abstract

Abstract The first (organo)catalytic method for regio- and chemoselective aza-Friedel–Crafts (FC) alkylation of indoles and pyrroles with commercially available methyl α-acetamidoacrylates has been discovered. It minimizes/eliminates common competing reactions that occur due to the high and multiatom-nucleophilic character of indole and pyrrole. Diverse quaternary α-amino acids were successfully prepared in good yield and high selectivity using low catalyst loading. The enantioselective variant using BINOL-derived phosphoric acids was also explored with indole providing the desired F–C alkylation product with moderate enantioselectivities.