铱催化的不对称烯丙基去芳构化反应通过去对称策略实现。
Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy.
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China.
出版信息
Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15093-15097. doi: 10.1002/anie.201708419. Epub 2017 Oct 24.
A desymmetrization strategy was developed involving iridium-catalyzed allylic dearomatization of indoles. The six-membered-ring spiroindolenines contain three contiguous stereogenic centers, including an all-carbon quaternary center, and were obtained in up to 99 % yield with 99 % ee and >95:5 d.r. When treated with a catalytic amount of tosylic acid, six-membered spiroindolenine undergoes an unprecedented six-to-seven-membered ring expansion, affording the corresponding hexahydroazepino[4,5-b]indole.
开发了一种不对称化策略，涉及铱催化吲哚的烯丙基去芳构化。六元环螺吲哚啉含有三个连续的手性中心，包括全碳季碳中心，以高达 99%的产率、99%的对映选择性和>95:5 的 dr 获得。当用催化量的对甲苯磺酸处理时，六元环螺吲哚啉经历了前所未有的六到七元环扩张，生成相应的六氢氮杂[4,5-b]吲哚。
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