Organocatalytic synthesis of N-Phenylisoxazolidin-5-ones and a one-pot synthesis of beta-amino acid esters

Org Lett. 2008 Mar 6;10(5):953-6. doi: 10.1021/ol800003n. Epub 2008 Feb 5.

Abstract

A novel N-heterocyclic carbene (NHC)-catalyzed C-N bond formation by the reaction of alpha,beta-unsaturated aldehydes and nitrosobenzene to N-phenylisoxazolidin-5-ones, followed by an acid-catalyzed esterification and Bamberger-like rearrangement in a mild one-pot protocol leads to N-p-methoxyphenyl (N-PMP) protected beta-amino acid esters.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Esterification
  • Esters
  • Molecular Structure
  • Nitrobenzenes / chemistry
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amino Acids
  • Esters
  • Nitrobenzenes
  • Oxazolidinones
  • nitrobenzene