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 E. Knezevic, Victoria Sun, Sharday Grant, Anna G. Wenzel

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

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 2010

Keywords

  • Asymmetric catalysis
  • Biaryls
  • Chiral resolution
  • Organocatalysis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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