title: Highly enantioselective construction of trifluoromethylated all-carbon quaternary stereocenters via nickel-catalyzed Friedel-Crafts alkylation reaction.
abstract: A highly enantioselective Friedel-Crafts alkylation reaction of indoles with β-CF(3)-β-disubstituted nitroalkenes was achieved using a Ni(ClO(4))(2)-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereocenters in good yields with excellent enantioselectivities (up to 97% ee). The transformation of one of the products into first a trifluoromethylated tryptamine and then a trifluoromethylated tetrahydro-β-carboline by sequential nitro reduction and Pictet-Spengler cyclization were realized with complete preservation of enantiopurity.
authors: College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, China.
authors: Jian-Rong
authors: JR
authors: Gao
authors: Hao
authors: H
authors: Wu
authors: Bin
authors: B
authors: Xiang
authors: Wu-Bin
authors: WB
authors: Yu
authors: Liang
authors: L
authors: Han
authors: Yi-Xia
authors: YX
authors: Jia
mesh_terms: D000478:Alkylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002244:Carbon; D009532:Nickel