Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione

Chem Commun (Camb). 2012 Dec 21;48(98):11978-80. doi: 10.1039/c2cc36807b.


The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in each case. Attempts at asymmetric transfer hydrogenation (ATH) of resulted in formation of a racemic product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Compounds / chemical synthesis*
  • Benzyl Compounds / chemistry
  • Hydrogenation
  • Molecular Structure
  • Piperidones / chemical synthesis*
  • Piperidones / chemistry*
  • Stereoisomerism


  • (3E)-1-benzyl-3-((2-oxopyridin-1(2H)-yl)methylidene)piperidine-2,6-dione
  • Benzyl Compounds
  • Piperidones
  • glutarimide