Asymmetric synthesis of biaryl atropisomers by dynamic resolution on condensation of biaryl aldehydes with (-)-ephedrine or a proline-derived diamine

Ann Bracegirdle, Jonathan Clayden*, Lai Wah Lai

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

11 Citations (Scopus)

Abstract

Atropisomeric biaryl aldehydes undergo diastereoselective condensation with (-)-ephedrine and with a proline-derived diamine, with selectivity highly dependent on solvent, temperature and reaction conditions. Levels of thermodynamic control up to 5:1 may be obtained by heating the diamine with the aldehyde in a sealed tube. Alternatively, crystallisation-induced dynamic transformation allows isolation of a single diastereoisomer in up to 85% yield. Hydrolysis and reduction of the major diastereoisomeric product of the reaction yields atropisomeric biaryls in >99:1 enantiomeric ratios.

Original languageEnglish
Article number47
JournalBeilstein Journal of Organic Chemistry
Volume4
Issue number47
DOIs
Publication statusPublished - 4 Dec 2008

Keywords

  • Atropisomer
  • Biaryl
  • Dynamic resolution
  • Ephedrine
  • Imdazolidine
  • Oxazolidine

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