at Google ScholarTitle data
Breuning, Matthias ; Häuser, Tobias ; Mehler, Christian ; Däschlein, Christian ; Strohmann, Carsten ; Oechsner, Andreas ; Braunschweig, Holger:
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0²,⁶]decane skeleton.
In: Beilstein Journal of Organic Chemistry.
Vol. 5
(2009)
.
- 81.
ISSN 1860-5397
DOI: https://doi.org/10.3762/bjoc.5.81
Abstract in another language
An enantioselective route to four tricyclic amino acids and N-tosylamides, composed of a central norbornane framework with a 2-endo,3-endo-annelated pyrrolidine ring and a 5-endo-C1 or -C2 side chain, has been developed. A key intermediate was the chiral, N-Boc-protected ketone (1R,2S,6S,7R)-4-azatricyclo[5.2.1.02,6]decan-8-one, available from inexpensive endo-carbic anhydride in five steps and 47% yield. The rigid scaffold makes these amino acid derivatives promising candidates for β-turn-inducing building blocks in peptidomimetics and for chiral auxiliaries in asymmetric organocatalysis.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | amino acid; enantioselective synthesis; norbornane; polycyclic compounds; pyrrolidine |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry III - Naturstoffsynthese und Katalyse > Professor Organic Chemistry III - Naturstoffsynthese und Katalyse - Univ.-Prof. Dr. Matthias Breuning Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry III - Naturstoffsynthese und Katalyse |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 11 Jan 2022 13:50 |
| Last Modified: | 20 Sep 2024 12:29 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68310 |