A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives
NEW JOURNAL OF CHEMISTRY, cilt.27, sa.1, ss.14-17, 2003 (SCI-Expanded, Scopus)
- 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.