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

Date

2003-01-01

Author

BOLM, CARSTEN
SCHİFFERS, INGO
ATODİRESEİ, IULİANA
Özçubukçu, Salih
RAABE, GERHARD

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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.

Subject Keywords

Materials Chemistry, General Chemistry, Catalysis

URI

https://hdl.handle.net/11511/37722

Journal

NEW JOURNAL OF CHEMISTRY

DOI

https://doi.org/10.1039/b206943c

Collections

Department of Chemistry, Article

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Citation Formats

C. BOLM, I. SCHİFFERS, I. ATODİRESEİ, S. Özçubukçu, and G. RAABE, “A novel asymmetric synthesis of highly enantiomerically enriched norbornane-type diamine derivatives,” NEW JOURNAL OF CHEMISTRY, pp. 14–17, 2003, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/37722.