Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

Beilstein J Org Chem. 2016 Apr 15:12:725-31. doi: 10.3762/bjoc.12.72. eCollection 2016.

Abstract

A highly enantioselective α-amination of 3-substituted oxindoles with azodicarboxylates catalyzed by amino acids-derived chiral phosphine catalysts is reported. The corresponding products containing a tetrasubstituted carbon center attached to a nitrogen atom at the C-3 position of the oxindole were obtained in high yields and with up to 98% ee.

Keywords: 3-aminooxindoles; asymmetric catalysis; phosphine catalyst; tetrasubstituted stereogenic carbon centers.