Synthesis of Multisubstituted Allenes by Palladium-Catalyzed Carboetherification of β,γ-Unsaturated Ketoximes with Propargylic Acetates

Org Lett. 2023 Jun 30;25(25):4682-4687. doi: 10.1021/acs.orglett.3c01561. Epub 2023 Jun 19.

Abstract

A highly efficient Pd-catalyzed carboetherification reaction of β,γ-unsaturated ketoximes with propargylic acetates is demonstrated. This method provides a practical protocol for accessing the incorporation of an allene moiety into 3,5-disubstituted and 3,5,5-trisubstituted isoxazolines. The salient features of this transformation include a broad substrate scope, good functional group tolerance, an easy scale-up, versatile transformations, and applications in the late-stage modification of drugs.

MeSH terms

  • Acetates
  • Catalysis
  • Oximes*
  • Palladium*

Substances

  • Palladium
  • propadiene
  • Oximes
  • Acetates