Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis

Elisa G. Gutierrez, Eric J. Moorhead, Eva H. Smith, Vivian Lin, Laura K.G. Ackerman, Claire Knezevic, Victoria Sun, Sharday Grant, Anna G. Wenzel

Research output: Contribution to journalArticle

Abstract

Facile synthetic routes to a chiral chloro-substituted biphenyl-2,2′- diyl hydrogen phosphate and a chiral O,O-biphenyl-2,2′-diyl phosphoramidothioate are described. The performance of these compounds as catalysts for the hydrophosphorylation of imines and the Friedel-Crafts alkylation of indole was investigated. In the latter reaction, the chlorosubstituted phosphoric acid derivative was found to rival the best Bronsted acid catalysts reported to date.

Original languageEnglish (US)
Pages (from-to)3027-3031
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
StatePublished - Jun 1 2010
Externally publishedYes

Fingerprint

Catalysis
catalysis
catalysts
Catalysts
Imines
Electrons
phosphoric acid
alkylation
indoles
Alkylation
imines
Hydrogen
phosphates
vehicles
electrons
Phosphates
routes
Derivatives
acids
Acids

Keywords

  • Asymmetric catalysis
  • Biaryls
  • Chiral resolution
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Gutierrez, E. G., Moorhead, E. J., Smith, E. H., Lin, V., Ackerman, L. K. G., Knezevic, C., ... Wenzel, A. G. (2010). Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis. European Journal of Organic Chemistry, (16), 3027-3031. https://doi.org/10.1002/ejoc.201000070

Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis. / Gutierrez, Elisa G.; Moorhead, Eric J.; Smith, Eva H.; Lin, Vivian; Ackerman, Laura K.G.; Knezevic, Claire; Sun, Victoria; Grant, Sharday; Wenzel, Anna G.

In: European Journal of Organic Chemistry, No. 16, 01.06.2010, p. 3027-3031.

Research output: Contribution to journalArticle

Gutierrez, EG, Moorhead, EJ, Smith, EH, Lin, V, Ackerman, LKG, Knezevic, C, Sun, V, Grant, S & Wenzel, AG 2010, 'Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis', European Journal of Organic Chemistry, no. 16, pp. 3027-3031. https://doi.org/10.1002/ejoc.201000070
Gutierrez, Elisa G. ; Moorhead, Eric J. ; Smith, Eva H. ; Lin, Vivian ; Ackerman, Laura K.G. ; Knezevic, Claire ; Sun, Victoria ; Grant, Sharday ; Wenzel, Anna G. / Electron-withdrawing, bipheny 1-2,2 -diol-based compounds for asymmetric catalysis. In: European Journal of Organic Chemistry. 2010 ; No. 16. pp. 3027-3031.
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AU - Lin, Vivian

AU - Ackerman, Laura K.G.

AU - Knezevic, Claire

AU - Sun, Victoria

AU - Grant, Sharday

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