Asymmetric synthesis of oxazolines bearing α-stereocenters through radical addition-enantioselective protonation enabled by cooperative catalysis

An efficient radical conjugate addition/enantioselective protonation process was developed for N-aryl glycines and alkenyl oxazolines enabled by the cooperative photoredox catalysis and chiral phosphoric acid catalysis, which generated a series of chiral oxazolines bearing an alpha-stereocenter with high enantioselectivities. The facile transformations of the chiral oxazoline products into enantioenriched lactams and gamma-amino esters bearing alpha-stereocenters demonstrate the value of this method.

Automated summary

An efficient radical conjugate addition/enantioselective protonation process was developed for N-aryl glycines and alkenyl oxazolines enabled by cooperative photoredox catalysis and chiral phosphoric acid catalysis, leading to a series of chiral oxazolines with high enantioselectivities. The facile transformations of the chiral oxazoline products into enantioenriched lactams and gamma-amino esters with alpha-stereocenters demonstrate the value of this method.