Ligand-Controlled Diastereoselective 1,3-Dipolar Cycloadditions of Azomethine Ylides with Methacrylonitrile

Org Lett. 2015 Dec 18;17(24):6166-9. doi: 10.1021/acs.orglett.5b03171. Epub 2015 Nov 25.

Abstract

Copper-catalyzed reactions of glycine ester arylimines and methacrylonitrile provide selective access to either the endo or exo pyrrolidine cycloadducts. DFT calculations have elucidated the origins of ligand-controlled diastereoselectivity.

Publication types

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

MeSH terms

  • Azo Compounds / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry
  • Cycloaddition Reaction
  • Glycine / analogs & derivatives
  • Glycine / chemistry
  • Ligands
  • Methacrylates / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Stereoisomerism
  • Thiosemicarbazones / chemistry*

Substances

  • Azo Compounds
  • Ligands
  • Methacrylates
  • Nitriles
  • Pyrrolidines
  • Thiosemicarbazones
  • azomethine
  • methacrylonitrile
  • Copper
  • Glycine