at Google ScholarTitle data
Breuning, Matthias ; Steiner, Melanie:
Enantioselective Synthesis of 2-Phenyl-9-oxabispidines.
In: Synthesis.
(2007)
Issue 11
.
- pp. 1702-1706.
ISSN 0039-7881
DOI: https://doi.org/10.1055/s-2007-966040
Abstract in another language
A small selection of enantiomerically pure 2-phenyl-9-oxabispidines was synthesized in a three to five step procedure from commercially available starting materials. Ring opening of (R,R)-3-phenylglycidol with benzylamine, condensation with (S)-epichlorohydrin to the corresponding cis-2,6-bis(hydroxymethyl)-substituted morpholine intermediate, and final cyclization with a primary amine delivered the desired 2-phenyl-9-oxabispidines in good yields. The substituents at the nitrogen atoms were varied by debenzylation and subsequent alkylation.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | 9-oxabispidines; stereoselective synthesis; bicyclic compounds; heterocycles; sparteine |
| 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 14:43 |
| Last Modified: | 11 Jan 2022 14:43 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68319 |