Copper-Catalyzed Remote Regio- and Enantioselective Yne-Allylic Substitution of Coumarins.

Autor: Yin T; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Zhao C; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Yao C; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Qian HD; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Yuan Z; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Peng H; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China., Feng Y; Engineering Research Center of Natural Cosmeceuticals College of Fujian Province, Department of Public Health and Medical Technology, Xiamen Medical College, 1999 Guankou Middle Road, Xiamen 361023, P. R. China., Xu H; Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jul 19; Vol. 26 (28), pp. 5961-5965. Date of Electronic Publication: 2024 Jul 10.
DOI: 10.1021/acs.orglett.4c02012
Abstrakt: Chiral coumarins and their derivatives are prominent bioactive structural units present in a wide range of natural products and pharmaceutical candidates. Therefore, the development of straightforward and efficient methodologies for the synthesis of readily functionalized chiral coumarins is of significant interest. Herein we report an enantioselective copper-catalyzed yne-allylic substitution of coumarins, resulting in a highly regioselective synthesis of diverse new classes of chiral coumarin derivatives with high efficiency and excellent functional group tolerance. Subsequent versatile transformations further demonstrate the substantial synthetic potential of this strategy in the field of biochemical research.
Databáze: MEDLINE