4.7 Article

Lewis Acid Catalyzed Friedel-Crafts Alkylation of Alkenes with Trifluoropyruvates

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JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 9, 页码 3929-3935

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00358

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资金

  1. National Natural Science Foundation of China [21372202, 21522207]
  2. Program for New Century Excellent Talents in University [NCET-12-1086]
  3. Natural Science Foundation of Zhejiang Province [LR14B020001]

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A Friedel-Crafts alkylation reaction of styrenes with trifluoropyruvates has been developed, which delivered allylic alcohols in excellent yields (up to 98%) using the Ni(ClO4)(2)center dot 6H(2)O/bipyridine complex as a catalyst. The asymmetric reaction was catalyzed by the chiral Cu(OTf)(2)/bisoxazoline complex to afford the corresponding chiral allylic alcohols bearing trifluoromethylated quaternary stereogenic centers in moderate enantioselectivities (up to 75% ee).

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