4.7 Article

Iridium-Catalyzed Intramolecular Enantioselective C-H Alkylation at the C-2 Position of N-Alkenylindoles

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 6, Pages 1131-1135

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201401163

Keywords

alkylation; C-H activation; enantioselectivity; indoles; iridium catalysts

Funding

  1. MEXT
  2. JST
  3. ACT-C
  4. Grants for Excellent Graduate School (Practical Chemical Wisdom), Waseda University, and MEXT, Japan
  5. Grants-in-Aid for Scientific Research [25105748] Funding Source: KAKEN

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Intramolecular enantioselective alkylation of N-alkenylindoles proceeded via C-H bond cleavage at the C-2 position in the presence of a cationic iridium catalyst with a diphosphine ligand. Aroyl groups at the C-3 position of the indoles operated as effective directing groups, and chiral 1-substituted-2,3-dihydro-1H-pyrrolo[1,2-a] indoles were obtained in high yield with excellent ee.

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