New, optically active phosphine oxazoline (JM-Phos) ligands: syntheses and applications in allylation reactions. Academic Article uri icon


  • Three different syntheses of the phosphine oxazoline systems 1 are presented. Two of these approaches are divergent routes designed to involve an advanced intermediate that can be transformed into several different end-products. The third is a shorter route specifically designed to facilitate preparations of these systems on a larger scale using minimal functional group protection. Overall, eight different phosphine oxazolines were prepared. These were screened in several palladium-mediated allylation reactions. They proved to be most useful for asymmetric alkylation of 3-acetoxy-1,3-diphenylpropene and less suitable/effective for the more challenging substrates (a pentenyl derivative and a cyclohexenyl system). X-ray crystallographic analysis of the complex [(eta 3-PhCHCHCHPh)Pd(1a)][PF6] led to the conclusion that the origins of asymmetric induction in these systems might be indirectly attributed to interaction of the oxazoline-phenyl substituent with the palladium and with an allyl-phenyl substituent. Finally, data is presented for allylation of a silylenolate of an N-acyl oxazolidinone; excellent enantioselectivities and yields were obtained.

published proceedings

  • J Org Chem

altmetric score

  • 6

author list (cited authors)

  • Hou, D. R., Reibenspies, J. H., & Burgess, K.

citation count

  • 94

complete list of authors

  • Hou, DR||Reibenspies, JH||Burgess, K

publication date

  • January 2001