Synthesis of a conformationally stable atropisomeric pair of biphenyl scaffold containing additional stereogenic centers

Chi Tung Yeung, Wesley Ting Kwok Chan, Wai Sum Lo, Ga Lai Law, Wing Tak Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

1 Citation (Scopus)

Abstract

The synthesis of a new CF3-containing stereogenic atropisomeric pair of ortho-disubstituted biphenyl scaffold is presented. The atropisomers are surprisingly conformationally stable for isolation. X-ray structures show that their stability comes from an intramolecular hydrogen bond formation from their two hydroxyl groups and renders the spatial arrangement of their peripheral CF3 and CH3 groups very different. The synthesized stereogenic scaffold proved to be effective in catalyzing the asymmetric N-nitroso aldol reaction of enamine and nitrosobenzene. Compared to similar scaffolds without CF3 groups, one of our atropisomer exhibits an increase in enantioselectivity in this reaction.

Original languageEnglish
Article number643
JournalMolecules
Volume24
Issue number3
DOIs
Publication statusPublished - 12 Feb 2019

Keywords

  • Asymmetry
  • Atropisomer
  • Hydrogen bond
  • N-nitroso aldol reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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