A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives


BOLM C., SCHİFFERS I., ATODİRESEİ I., Ozcubukcu S. , RAABE G.

NEW JOURNAL OF CHEMISTRY, vol.27, no.1, pp.14-17, 2003 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 1
  • Publication Date: 2003
  • Doi Number: 10.1039/b206943c
  • Title of Journal : NEW JOURNAL OF CHEMISTRY
  • Page Numbers: pp.14-17

Abstract

The simple and highly enantioselective methanolysis of norbornene dicarboxylic acid anhydride mediated by quinidine leads to the corresponding cis-monomethyl ester with 98% ee. By means of selective ester epimerization, followed by Curtius degradation of the intermediate trans-diacyl azide, two optically active norbornane-type diamines are obtained as their hydrochloric salts. Liberating the amine with an excess of triethylamine in situ and subsequent derivatization affords potential C-1-symmetric ligands for asymmetric catalysis in excellent yields.