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P-stereogenic wide bite angle diphosphine ligands

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Author(s)

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

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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.
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Details

Original languageEnglish
Pages (from-to)47-56
JournalTetrahedron
Volume75
Issue number1
Early online date14 Nov 2018
DOIs
Publication statusPublished - 3 Jan 2019

    Research areas

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

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