A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives
NEW JOURNAL OF CHEMISTRY, vol.27, no.1, pp.14-17, 2003 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Volume: 27 Issue: 1
- Publication Date: 2003
- Doi Number: 10.1039/b206943c
- Journal Name: NEW JOURNAL OF CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.14-17
- Middle East Technical University Affiliated: No
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.