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Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.

Publication ,  Journal Article
Liu, C; Widenhoefer, RA
Published in: Organic letters
May 2007

Treatment of 2-allenyl indole 4 with a catalytic 1:2 mixture of [(S)-2]Au2Cl2 [(S)-2 = (S)-3,5-tBu-4-MeO-MeOBIPHEP] and AgBF4 in toluene at -10 degrees C for 17 h led to isolation of tetrahydrocarbazole 5 in 88% yield with 92% ee. The protocol was effective for the cyclization of terminally disubstituted allenes and for the formation of seven-membered rings.

Duke Scholars

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Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

May 2007

Volume

9

Issue

10

Start / End Page

1935 / 1938

Related Subject Headings

  • Stereoisomerism
  • Solvents
  • Silver
  • Organic Chemistry
  • Molecular Structure
  • Ligands
  • Indoles
  • Hydrogen
  • Gold
  • Catalysis
 

Citation

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Liu, C., & Widenhoefer, R. A. (2007). Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles. Organic Letters, 9(10), 1935–1938. https://doi.org/10.1021/ol070483c
Liu, Cong, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.Organic Letters 9, no. 10 (May 2007): 1935–38. https://doi.org/10.1021/ol070483c.
Liu C, Widenhoefer RA. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles. Organic letters. 2007 May;9(10):1935–8.
Liu, Cong, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles.Organic Letters, vol. 9, no. 10, May 2007, pp. 1935–38. Epmc, doi:10.1021/ol070483c.
Liu C, Widenhoefer RA. Gold(I)-catalyzed intramolecular enantioselective hydroarylation of allenes with indoles. Organic letters. 2007 May;9(10):1935–1938.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

May 2007

Volume

9

Issue

10

Start / End Page

1935 / 1938

Related Subject Headings

  • Stereoisomerism
  • Solvents
  • Silver
  • Organic Chemistry
  • Molecular Structure
  • Ligands
  • Indoles
  • Hydrogen
  • Gold
  • Catalysis