Recently, research team of Professor Shi Feng from School of Chemistry & Materials Science has published a research paper titling “Atroposelective Access to Oxindole-Based Axially Chiral Styrenes via the Strategy of Catalytic Kinetic Resolution” (DOI: 10.1021/jacs.0c00208) in Journal of the American Chemical Society.
“Atroposelective synthesis of axiallychiral molecules has attracted substantial attention from chemists because ofthe importance of such molecules. However, catalytic asymmetric synthesis of axially chiral styrenes or vinyl arenes is underdeveloped and challenging due to the low rotational barrier and weak configurational stability of such molecules. Therefore, the development of powerful strategies for the catalyticatropo selective synthesis of axially chiral styrenes or vinyl arenes is of great importance.”
This work has accomplished the first atroposelective access to oxindole-based axially chiral styrenes by the strategy of catalytic kinetic resolution, and this strategy offered two kinds of oxindole-based axially chiral styrene derivatives in good diastereo selectivities (up to 94:6 dr) and excellent enantio selectivities (upto 98% ee) with high selectivity factors (S up to 106).
“This strategy not only provides easy access to oxindole-based axially chiral styrenes but also offers a robust method for synthesizing bisamide derivatives bearing both axial and central chirality. More importantly, this strategy has added a new class of members to the atropisomeric family, especially to the family of axially chiral styrenes.”
Ma Chun and Sheng Fengtao, postgraduate students from School of Chemistry & Materials Science are co-first authors. Prof. Shi Feng, Associate Prof. Zhang Yuchen and Dr. Tan Wei are co-corresponding authors, with Jiangsu Normal University as the affiliating unit.
The Journal of the American Chemical Society (JACS), founded in 1879, is the flagship journal of the American Chemical Society and the world's preeminent journal in all of chemistry and interfacing areas of science. This periodical is devoted to the publication of fundamental research papers and publishes approximately 19,000 pages of Articles, Communications, and Perspectives a year. Published weekly, JACS provides research essential to the field of chemistry.