Pd(II)-Catalyzed Atroposelective C-H Allylation: Synthesis of Enantioenriched N-Aryl Peptoid Atropisomers

A Pd-catalyzed atroposelective C-H allylation with 1,1-disubstituted alkenes was developed for the synthesis of enantioenriched N-aryl peptoid atropisomers via beta-H elimination using commercially available and inexpensive L-pGlu-OH as a chiral ligand. Exclusive allylic selectivity was achieved. Additionally, a series of enantioenriched N-aryl peptoid atropisomers were obtained in synthetically useful yields with excellent enantioselectivities (up to 90% yield and 97% ee).

Automated summary

A Pd-catalyzed atroposelective C-H allylation with 1,1-disubstituted alkenes was carried out using the chiral ligand L-pGlu-OH, resulting in the synthesis of enantioenriched N-aryl peptoid atropisomers. High yields and excellent enantioselectivities were achieved, with up to 90% yield and 97% ee.