Palladium-catalyzed carbenoid based N-H bond insertions: application to the synthesis of chiral α-amino esters

Org Biomol Chem. 2013 Sep 28;11(36):5998-6002. doi: 10.1039/c3ob41331d.

Abstract

A highly efficient palladium-catalyzed carbenoid based N-H bond insertion has been developed. The α-amino esters were obtained in high isolated yields. Moreover, by choosing a suitable chiral auxiliary, stereoselective Pd-catalyzed N-H insertion has been realized. The chiral α-amino esters were obtained in high yields (up to 91%) and with excellent diastereoselectivities (d.r. > 19 : 1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Esters / chemical synthesis*
  • Esters / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Esters
  • Organometallic Compounds
  • carbene
  • Palladium
  • Methane