The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry.We report a highly chemoselective and stereoselective casc...The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry.We report a highly chemoselective and stereoselective cascade cycloadditions of newly designed oxazepino indolones with 5-methylene-1,3-dioxanones,employing an iridium catalyst in combination with the Carreira ligand for the divergent synthesis of chiral polycyclic spiroindolines.This strategy enables the construction of a series of pentacyclic spiroindolines featuring two chiral quaternary stereocenters and one tertiary stereocenter in good yields with excellent chemoselectivity and stereocontrol(30 examples,up to 81%yield,>20:1 dr,99%ee).The process was scalable,and synthetic transformations of the products were performed to demonstrate their practical utility.展开更多
基金support for this work from the National Natural Science Foundation of China(21901142,22201161)the Natural Science Foundation of Shandong Province(ZR2024MB004,ZR2022QH294)+4 种基金the Medical and Health Science and Technology Development Program of Shandong Province(202102070368)the Fundamental Research Funds of Shandong University(2020QNQT007 and 2020QNQT009)Funded by Basic Research Program of Jiangsu(BK20220097)Open Research Fund Program of Key Laboratory of Marine Drugs,Ministry of Education(Ocean University of China,MDME2308-03)the Open Project of Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development(2024GCUKLACTRD003).
文摘The asymmetric construction of polycyclic spiroindolines featuring one or more quaternary stereocenters remains a significant challenge in synthetic chemistry.We report a highly chemoselective and stereoselective cascade cycloadditions of newly designed oxazepino indolones with 5-methylene-1,3-dioxanones,employing an iridium catalyst in combination with the Carreira ligand for the divergent synthesis of chiral polycyclic spiroindolines.This strategy enables the construction of a series of pentacyclic spiroindolines featuring two chiral quaternary stereocenters and one tertiary stereocenter in good yields with excellent chemoselectivity and stereocontrol(30 examples,up to 81%yield,>20:1 dr,99%ee).The process was scalable,and synthetic transformations of the products were performed to demonstrate their practical utility.
