The regioselective Wacker oxidation of internal allylamines: synthesis of functionalized and challenging β-amino ketones

Org Biomol Chem. 2022 Dec 21;21(1):115-126. doi: 10.1039/d2ob01843h.

Abstract

A convenient and general protocol for the palladium-catalysed oxidation of internal allylamine derivatives to β-amino ketones is reported. The transformation occurs at room temperature and shows a wide substrate scope as well as high functional group and N-protecting group tolerance. We also describe potential applications of the method, e.g., the synthesis of bioactive molecules or simple transformations of selected β-amino ketones into other interesting building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylamine*
  • Catalysis
  • Ketones* / chemistry
  • Oxidation-Reduction
  • Palladium / chemistry

Substances

  • Ketones
  • Allylamine
  • Palladium