Recently, Professor Shi Feng and Associate Professor Zhang Yuchen from School of Chemistry and Materials Science have made an important progress in Catalytic Asymmetric Construction of Indole-Based Scaffolds. The achievement was published in the internationally renowned journal Angewandte Chemie International Edition, entitled Organocatalytic Enantioselective Synthesis of Axially Chiral N, N’-Bisindoles. Jiangsu Normal University is the first signature unit and Chen Zhihan and Li Tianzhen are the co-first authors of the paper. Both of them are graduate students of our university. Professor Shi Feng and Associate Professor Zhang Yuchen are the co-corresponding authors. The paper was funded by the National Natural Science Foundation of China and the Natural Science Foundation of Jiangsu Province.
Axially chiral indole-based scaffolds are widely found in natural products, bioactive compounds, chiral catalysts or ligands, and functional materials. Therefore, catalytic asymmetric construction of indole-based scaffolds has aroused extensive interest in the chemical and biochemical community. N-N axially chiral bisindoles are an important type of axially chiral indole-based scaffolds, however, the catalytic atroposelective synthesis of such molecules remains largely unexplored. As the area for the 2021 Nobel Prize in Chemistry, organocatalysis has become an efficient strategy for asymmetric synthesis of chiral molecules. Feng Shi, Yu-Chen Zhang and co-workers performed the first organocatalytic asymmetric synthesis of axially chiral N, N’-bisindoles. The catalytic asymmetric formal (3+2) cycloadditions involving indole and pyrrole-based enaminones as a new type of platform molecules were carried out to afford various axially chiral N, N’-bisindoles in good yields and with excellent enantioselectivities. Besides, this class of axially chiral N, N’-bisindoles exhibited some degree of cytotoxicity toward cancer cells. More importantly, these axially chiral N, N’-bisindoles could also be derived into axially chiral catalysts and ligands, which have found high catalytic activity in asymmetric catalysis.. This study not only provides a new strategy for enantioselective synthesis of axially chiral N, N’-bisindoles via asymmetric organocatalysis but is also the first attempt to investigate the potential applications of axially chiral N, N’-bisindoles in asymmetric catalysis and medicinal chemistry, thereby solving previous issues in enantioselective construction and the application of N-N axially chiral bisindole scaffolds.
Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.202300419
Professor Shi Feng (https://www.x-mol.com/groups/Shi_Feng) is mainly engaged in the research of catalytic asymmetric synthesis of chiral heterocycles, focusing on chiral indole chemistry. She provides an efficient and highly selective method for the construction of complex and diverse chiral heterocyclic scaffolds. She has published 130 papers as a corresponding author on peer-reviewed international journals such as Acc. Chem. Res., J. Am. Chem. Soc., Angew. Chem. Int. Ed., Chin. J. Chem., Sci. China Chem. and Fund. Res.and has been selected as one of Elsevier’s 2020 and 2021 Highly Cited Researchers. Prof. Shi has been nominated as one of the “Top Ten Graduate Student Supervisors” in Jiangsu Province, achieved the Outstanding Award of Jiangsu Province Graduate Education Reform Achievement, the Second Prize of Science and Technology of Jiangsu Province, the Second Prize of Natural Science Award of the Chinese Ministry of Education, Thieme Chemistry Journal Award, the Asian Core Program Lectureship Award, NHU-CJC Innovation Award, etc. She is a member of editorial board for Chin. J. Org. Chem., Chem. Synth., and Eur. J.Org. Chem.She also works as a member of international advisory board for Org. Chem. Front., J. Org. Chem. and Synthesis.
Associate Professor Zhang Yuchen (http://chem.jsnu.edu.cn/64/d4/c15352a287956/page.htm) is mainly engaged in the research of catalytic asymmetric construction of chiral bioactive scaffolds. In recent years, he has published as the first author or corresponding author in important scientific journals such as Acc. Chem.Res., J. Am. Chem. Soc., Angew. Chem. Int. Ed., Chin. J. Chem., Sci. China Chem., Org. Chem. Front., Org. Lett. etc. Also, Prof. Zhang has authorized 8 patents for invention.