Catalytic enantioselective synthesis of atropisomeric 2-aryl-4-quinolinone derivatives with an N-C chiral axis

摘要

In the presence of an (R)-MOP-Pd_2(dba)_3 catalyst, the reaction of ortho-tert-butylaniline with 2-bromophenyl arylethynyl ketone proceeded via a tandem amination (1,4-addition of aniline to an ynone and subsequent intramolecular Buchwald-Hartwig amination) to afford axially chiral N-(2-tert-butylphenyl)-2-aryl-4-quinolinone derivatives with moderate enantioselectivity (up to 72% ee).