Control of enantioselectivity in the photochemical conversion of alpha-oxoamides into beta-lactam derivatives

Org Lett. 2002 May 2;4(9):1443-6. doi: 10.1021/ol025700i.

Abstract

[reaction: see text]. Several approaches to asymmetric induction in the alpha-oxoamide (1) to beta-lactam (2) photorearrangement are described. Best results are obtained via irradiation of ionic and covalent chiral auxiliary-containing reactants in the crystalline state and in the interior supercages of zeolites.

Publication types

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

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Crystallography, X-Ray
  • Cyclodextrins
  • Keto Acids / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Oxamic Acid / analogs & derivatives*
  • Oxamic Acid / chemical synthesis*
  • Oxamic Acid / chemistry
  • Photochemistry
  • Stereoisomerism
  • Zeolites
  • beta-Lactams

Substances

  • Anti-Bacterial Agents
  • Cyclodextrins
  • Keto Acids
  • beta-Lactams
  • Zeolites
  • Oxamic Acid