Alpha,gamma-diamino acids: asymmetric synthesis of new constrained 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids

J Org Chem. 2006 Oct 27;71(22):8467-72. doi: 10.1021/jo061391o.

Abstract

The synthesis of two new diastereomeric 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids exo- and endo-8,9 is reported using exo- and endo-norbornene amino acids as chiral building blocks. This method provides a fast access to optically pure amino acids 8 and 9 which can be considered both alpha,gamma- and alpha,delta-diamino acids containing sterical constraints and characterized by alpha,alpha-disubstitution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids, Diamino / chemical synthesis*
  • Amino Acids, Diamino / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Molecular Structure
  • Norbornanes / chemistry
  • Stereoisomerism
  • Time Factors

Substances

  • Amino Acids, Diamino
  • Bridged Bicyclo Compounds, Heterocyclic
  • Carboxylic Acids
  • Norbornanes