Functionalized azabicycloalkane amino acids by nitrone 1,3-dipolar intramolecular cycloaddition

J Org Chem. 2005 May 13;70(10):4124-32. doi: 10.1021/jo0500683.

Abstract

[reaction: see text] An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemical synthesis*
  • Alkanes / chemistry
  • Alkanes / metabolism
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Amino Acids / metabolism
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Aza Compounds / metabolism
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / metabolism
  • Cross-Linking Reagents / chemistry
  • Cyclization
  • Molecular Mimicry
  • Nitrogen Oxides / chemistry*
  • Stereoisomerism

Substances

  • Alkanes
  • Amino Acids
  • Aza Compounds
  • Bridged Bicyclo Compounds, Heterocyclic
  • Cross-Linking Reagents
  • Nitrogen Oxides
  • nitrones