Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: synthesis of β-vinyl α-amino acids

Org Lett. 2014 Dec 5;16(23):6260-3. doi: 10.1021/ol503248f. Epub 2014 Nov 20.


A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp(3))-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp(3))-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

Publication types

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

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis*
  • Alanine / chemistry
  • Alkenes / chemical synthesis*
  • Alkenes / chemistry*
  • Catalysis
  • Molecular Structure
  • Palladium / chemistry*
  • Stereoisomerism
  • Temperature
  • Vinyl Compounds / chemistry*


  • Alkenes
  • Vinyl Compounds
  • vinyl iodide
  • Palladium
  • Alanine