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Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate |
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| Authors: | Lu Ding Dr Run-Duo Gao Prof Dr Shu-Li You |
| Institution: | 1. School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210 P. R. China;2. 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 P. R. China |
| Abstract: | An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee) and chemoselectivity ( 3 / 4 >19:1 in most cases). |
| Keywords: | allylic compounds asymmetric catalysis cascade reactions dearomatization palladium |