New, optically active phosphine oxazoline (JM-phos) ligands: Syntheses and applications in allylation reactions

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

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Abstract

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 [(η3-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.

Original languageEnglish
Pages (from-to)206-215
Number of pages10
JournalJournal of Organic Chemistry
Volume66
Issue number1
DOIs
StatePublished - 12 Jan 2001

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