Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement

J Org Chem. 2022 Mar 4;87(5):2947-2958. doi: 10.1021/acs.joc.1c02804. Epub 2022 Feb 10.


We disclose here practical strategies toward the synthesis of morpholines and Claisen rearrangement products based on the divergent reactivity of a common halonium intermediate. These reactions employ widely available alkenes in a Lewis acid-catalyzed halo-etherification process that can then transform them into the desired products with exceptional regioselectivity for both activated and unactivated olefins. Our mechanistic probe reveals an interesting regiochemical kinetic resolution process.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes*
  • Catalysis
  • Lewis Acids*
  • Morpholines


  • Alkenes
  • Lewis Acids
  • Morpholines