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Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.0²,⁶]decane skeleton

Title 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) . - No. 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 > Professor Organic Chemistry - Univ.-Prof. Dr. Matthias Breuning
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 11 Jan 2022 13:50
Last Modified: 11 Jan 2022 13:50
URI: https://eref.uni-bayreuth.de/id/eprint/68310