Pd(II)-Catalyzed Atroposelective C–H Allylation: Synthesis of Enantioenriched <i>N</i>-Aryl Peptoid Atropisomers
Zhen‐Sheng Jia, Yong‐Jie Wu, Qi‐Jun Yao, Xue-Tao Xu, Kun Zhang, Bing‐Feng Shi
Abstract
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-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).
Topics & Concepts
AtropisomerChemistryArylPeptoidCatalysisCombinatorial chemistryStereochemistryOrganic chemistryPeptideAlkylBiochemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityCatalytic C–H Functionalization Methods