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, cilt.27, ss.14-17, 2003 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 27 Konu: 1
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1039/b206943c
  • Dergi Adı: NEW JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.14-17

Özet

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.