4.7 Article

H-Adamantylphosphinates as Universal Precursors of P-Stereogenic Compounds

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 8, Pages 4132-4141

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00548

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Funding

  1. CNRS
  2. Centrale Marseille
  3. Aix-Marseille University

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A new family of H-adamantylphosphinates as universal precursors of P-stereogenic ligands was obtained in one step from commercial chlorophosphines. Both enantiomers of these air- and moisture-stable intermediates can easily be separated by semipreparative chiral HPLC on a gram scale and individually undergo stereoselective transformations to afford each enantiomer of a set of P-stereogenic compounds such as secondary phosphine oxides and boron-protected monophosphines.

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