Enantioselective Coupling of Dienes and Phosphine Oxides

J Am Chem Soc. 2018 Dec 5;140(48):16450-16454. doi: 10.1021/jacs.8b11150. Epub 2018 Nov 19.

Abstract

We report a Pd-catalyzed intermolecular hydrophosphinylation of 1,3-dienes to afford chiral allylic phosphine oxides. Commodity dienes and air stable phosphine oxides couple to generate organophosphorus building blocks with high enantio- and regiocontrol. This method constitutes the first asymmetric hydrophosphinylation of dienes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkadienes / chemistry*
  • Allyl Compounds / chemical synthesis*
  • Catalysis
  • Chemistry Techniques, Synthetic / methods
  • Coordination Complexes / chemistry
  • Palladium / chemistry
  • Phosphines / chemical synthesis
  • Phosphines / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Allyl Compounds
  • Coordination Complexes
  • Phosphines
  • Palladium