Further studies on the [1,2]-Wittig rearrangement of 2-(2-benzyloxy)aryloxazolines

R Alan Aitken*, Andrew D. Harper, Ryan Inwood

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The behaviour of 14 ortho-functionalised 2-aryloxazolines, 11 of them prepared and characterised for the first time, with butyllithium has been examined. Significant limitations to the Wittig rearrangement of such systems are revealed. In terms of asymmetric Wittig rearrangement, good diastereoselectivity is obtained with a valine-derived 4-isopropyl oxazoline but this is compromised by racemisation upon hydrolysis. More encouraging selectivity is achieved in the Wittig rearrangement of an acyclic phenylalanine-derived ortho-benzyloxy benzamide.
Original languageEnglish
Article number3186
Number of pages23
Issue number10
Publication statusPublished - 17 May 2022


  • Oxazoline
  • Wittig rearrangement
  • Phthalide


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