Enantioselective Addition of Pyrazoles to Dienes*

Angew Chem Int Ed Engl. 2021 Sep 1;60(36):19660-19664. doi: 10.1002/anie.202105679. Epub 2021 Aug 1.

Abstract

We report the first enantioselective addition of pyrazoles to 1,3-dienes. Secondary and tertiary allylic pyrazoles can be generated with excellent regioselectivity. Mechanistic studies support a pathway distinct from previous hydroaminations: a Pd0 -catalyzed ligand-to-ligand hydrogen transfer (LLHT). This hydroamination tolerates a range of functional groups and advances the field of diene hydrofunctionalization.

Keywords: 1,3-diene; Pd-catalysis; enantioselectivity; hydroamination; pyrazole.

Publication types

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

MeSH terms

  • Alkadienes / chemistry*
  • Catalysis
  • Ligands
  • Molecular Structure
  • Palladium / chemistry
  • Pyrazoles / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Ligands
  • Pyrazoles
  • Palladium