Li Zhu, Zhang Pei-Xu, Li Zhao-Zhao, Zhang Xing-Lu, Cao Hong-Yuan, Gao Yu-Ning, Bian Ming, Chen Hui-Yu, Liu Zhen-Jiang
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai 201418, P. R. China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.
Org Lett. 2022 Sep 23;24(37):6863-6868. doi: 10.1021/acs.orglett.2c02830. Epub 2022 Sep 14.
A Brønsted acid catalyzed tandem process to access densely functionalized chromeno[3,2-]isoxazoles with good to excellent yields and diastereoselectivities was disclosed. The procedure is proposed to involve a 1,6-conjugate addition/electrophilic addition/double annulations process of alkynyl -quinone methides (-AQMs) in situ generated from -hydroxyl propargylic alcohols with nitrones. Mild conditions, good functional group compatibility, easy scale-up of the reaction, and further product transformation demonstrated its potential application.
公开了一种布朗斯特酸催化的串联反应过程，可用于制备具有良好至优异产率和非对映选择性的高度官能化色烯并[3,2 -]异恶唑。该过程被认为涉及由α-羟基炔丙醇与硝酮原位生成的炔基醌甲基化物（-AQMs）的1,6 -共轭加成/亲电加成/双环化过程。温和的条件、良好的官能团兼容性、易于放大反应以及进一步的产物转化证明了其潜在应用价值。
