4.8 Article

Chiral Holmium Complex-Catalyzed Diels-Alder Reaction of Silyloxyvinylindoles: Stereoselective Synthesis of Hydrocarbazoles

Journal

ORGANIC LETTERS
Volume 15, Issue 20, Pages 5314-5317

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol402559z

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Funding

  1. JSPS KAKENHI [22790007, 25460006, 21390002, 25293001]
  2. Takeda Science Foundation
  3. Grants-in-Aid for Scientific Research [25293001, 21390002, 22790007, 25460006] Funding Source: KAKEN

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The catalytic and asymmetric cycloaddition between 3[1-(silyloxy)vinyl]indoles and electron-deficient olefins gave substituted hydrocarbazoles in up to 99% yield and 94% ee. This reaction was catalyzed by a novel chiral holmium(III) complex. Alkylation of the cycloadduct gave a tricyclic compound with four continuous chiral centers, one of which was a quaternary carbon.

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