P-stereogenic wide bite angle diphosphine ligands

Christine F. Czauderna, Alexandra M. Z. Slawin, David B. Cordes, Jarl Ivar van der Vlugt, Paul C.J. Kamer

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)
7 Downloads (Pure)

Abstract

Two modular synthetic approaches for the preparation of novel wide bite angle diphosphine ligands containing stereogenic P-atoms have been developed, leading to compounds (S,S)-2,2′-bis(methylphenylphosphino)diphenyl ether (L1) and (S,S)-2,2′-bis(ferrocenylphenylphosphino)diphenyl ether (L2) in very good diastereomeric ratios. Both protocols involve diphenyl ether as backbone and (2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane (RP)-5 as initial auxiliary to induce chirality at phosphorus. The absolute configuration of intermediates (S,S)-9-(BH3)2 and (R,R)-10-(BH3)2 as well as the ligands (S,S)-L1-BH3 and (S,S)-L2 was determined by X-ray crystallographic analysis.
Original languageEnglish
Pages (from-to)47-56
JournalTetrahedron
Volume75
Issue number1
Early online date14 Nov 2018
DOIs
Publication statusPublished - 3 Jan 2019

Keywords

  • P-stereogenic ligand
  • Wide bite angle ligand
  • Ephedrine
  • Phosphinite borane
  • Oxazaphospholidine

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