Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes

J Am Chem Soc. 2017 Feb 8;139(5):1774-1777. doi: 10.1021/jacs.6b12307. Epub 2017 Jan 27.

Abstract

We communicate a strategy for the hydrofunctionalization of 1,3-dienes via Rh-hydride catalysis. Conjugated dienes are coupled to nucleophiles to demonstrate the feasibility of novel C-C, C-O, C-S, and C-N bond forming processes. In the presence of a chiral JoSPOphos ligand, hydroamination generates chiral allylic amines with high regio- and enantioselectivity. Tuning both the pKa and steric properties of an acid-additive is critical for enantiocontrol.

Publication types

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

MeSH terms

  • Alkadienes / chemistry*
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Catalysis
  • Indoles / chemistry*
  • Molecular Structure
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Amines
  • Indoles
  • indoline
  • Rhodium