Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton
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-azatr...
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Beilstein-Institut
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.5.81 |
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doaj-7439a4e28c684dd58105c8493d56af6c2021-03-02T11:11:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972009-12-01518110.3762/bjoc.5.811860-5397-5-81Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeletonMatthias Breuning0Tobias Häuser1Christian Mehler2Christian Däschlein3Carsten Strohmann4Andreas Oechsner5Holger Braunschweig6Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyInstitut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyInstitut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyAnorganische Chemie, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, GermanyAnorganische Chemie, Universität Dortmund, Otto-Hahn-Str. 6, 44227 Dortmund, GermanyInstitut für Anorganische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyInstitut für Anorganische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, GermanyAn 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.https://doi.org/10.3762/bjoc.5.81amino acidenantioselective synthesisnorbornanepolycyclic compoundspyrrolidine |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Matthias Breuning Tobias Häuser Christian Mehler Christian Däschlein Carsten Strohmann Andreas Oechsner Holger Braunschweig |
| spellingShingle |
Matthias Breuning Tobias Häuser Christian Mehler Christian Däschlein Carsten Strohmann Andreas Oechsner Holger Braunschweig Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton Beilstein Journal of Organic Chemistry amino acid enantioselective synthesis norbornane polycyclic compounds pyrrolidine |
| author_facet |
Matthias Breuning Tobias Häuser Christian Mehler Christian Däschlein Carsten Strohmann Andreas Oechsner Holger Braunschweig |
| author_sort |
Matthias Breuning |
| title |
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| title_short |
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| title_full |
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| title_fullStr |
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| title_full_unstemmed |
Enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| title_sort |
enantioselective synthesis of tricyclic amino acid derivatives based on a rigid 4-azatricyclo[5.2.1.02,6]decane skeleton |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2009-12-01 |
| description |
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. |
| topic |
amino acid enantioselective synthesis norbornane polycyclic compounds pyrrolidine |
| url |
https://doi.org/10.3762/bjoc.5.81 |
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