4.7 Article

SPINOL-Derived Phosphoric Acids: Synthesis and Application in Enantioselective Friedel-Crafts Reaction of Indoles with Imines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 24, Pages 8677-8680

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo101640z

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Funding

  1. National Natural Science Foundation of China [20872128, J0830413]
  2. Fundamental Research Funds for the Central Universities [2009QNA3011]
  3. Natural Science Foundation of Zhejiang Province [R407106]

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A new class of chiral phosphoric acids with spirobiindane s scaffold were conveniently synthesized from (S)-1,1'-spirobiindane-7,7'-diol ((S)-SPINOL) and employed to catalyze the asymmetric Friedel-Crafts reaction of in-doles with imines to afford 3-indolylmethanamines. High yields (68-97%) and excellent enantioselectivities (up to 99% ee) were obtained.

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