1337962-77-2Relevant academic research and scientific papers
Organocatalytic synthesis of α-quaternary amino acid derivatives via aza-Friedel-Crafts alkylation of indoles with simple α-amidoacrylates
Righi, Marika,Bartoccini, Francesca,Lucarini, Simone,Piersanti, Giovanni
, p. 7923 - 7928 (2011)
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.
