Regioselective α-Deuteration of Michael Acceptors Mediated by Isopropylamine in D 2 O/AcOD

Org Lett. 2020 Dec 18;22(24):9745-9750. doi: 10.1021/acs.orglett.0c03839. Epub 2020 Dec 1.

Abstract

Site-specific hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features D2O and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle motifs as well as enones. The method has been applied to the synthesis of deuterated drug precursors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Deuterium / chemistry*
  • Hydrogen / chemistry*
  • Molecular Structure
  • Propylamines / chemistry*

Substances

  • Amines
  • Propylamines
  • Hydrogen
  • Deuterium
  • 2-propylamine