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

Zhen-Sheng JiaYong-Jie WuQi-Jun YaoXue-Tao XuKun ZhangTimothy M Swager
Published in: Organic letters (2021)
A Pd-catalyzed atroposelective C-H allylation with 1,1-disubstituted alkenes was developed for the synthesis of enantioenriched N -aryl peptoid atropisomers via β-H elimination using commercially available and inexpensive L- p Glu-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).
Keyphrases
  • room temperature
  • ionic liquid
  • capillary electrophoresis