Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination

Due to the lower configuration stability of vinylarenes, arsing from the relatively lower rotational barriers, their catalytic asymmetric synthesis remains a daunting task. Oxindoles moiety are privileged framework of natural products and building blocks of bioactive molecules as well as pharmaceuticals. The asymmetric synthesis of axial chiral vinvlarenes fearturing oxindole moiety via sequential carbopalladation/C - H olefination from readily available materials with palladium catalysis has been developed. (4R,5R)-(-)-2,2-Dimethyl-alpha,alpha,alpha',alpha'-tetrapheny1-1,3-dioxolane-4,5-dimethanol (TADDOL)-derived phosphoramidite gave products with good yield and moderate ee value. The erosion of optical purity was not observed even after heating the product for 10 hat 110 V, which indicates the excellent stability of the chiral axial.