at Google ScholarTitle data
Breuning, Matthias ; Hein, David:
First asymmetric synthesis of a C₂-symmetric 2-endo,6-endo-disubstituted bispidine.
In: Tetrahedron: Asymmetry.
Vol. 18
(2007)
Issue 12
.
- pp. 1410-1418.
ISSN 0957-4166
DOI: https://doi.org/10.1016/j.tetasy.2007.06.010
Abstract in another language
The enantioselective synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane) has been accomplished for the first time. The key step was a Michael addition of the protected β-amino ester methyl (R)-3-{N-benzyl-N-[(S)-1-phenylethyl]amino}-3-phenylpropionate to its α-methylene derivative delivering an anti,anti-configured α,α′-methylene-bridged bis(β-amino ester) as the major diastereomer. Deprotection, reduction and cyclisation furnished (1R,2R,5R,6R)-2,6-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane in six steps and 15% overall yield.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| 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 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 |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 11 Jan 2022 14:30 |
| Last Modified: | 11 Jan 2022 14:30 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68317 |