4.8 Article

Organocatalyzed Enantioselective Formal [4+2] Cycloadclition of 2,3-Disubstituted Indole and Methyl Vinyl Ketone

Journal

ORGANIC LETTERS
Volume 14, Issue 12, Pages 3040-3043

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301114z

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Funding

  1. National Basic Research Program of China (973 Program) [2010CB833300]
  2. National Natural Science Foundation of China [20923005, 21025209, 21121062]
  3. Chinese Academy of Sciences

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A formal [4 + 2] cycloaddition of 2,3-disubstituted indoles with vinyl methyl ketone was realized in the presence of a catalytic amount of quinine-derived primary amine and pentafluorobenzoic acid. This method provides bridged-ring indoline scaffolds containing two quaternary carbon centers with excellent yields and enantioselectivity (up to 98% yield and 98% ee).

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