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, sa.1, ss.14-17, 2003 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 1
  • Basım Tarihi: 2003
  • Doi Numarası: 10.1039/b206943c
  • Dergi Adı: NEW JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.14-17
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

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.