at Google ScholarTitle data
Scharnagel, Dagmar ; Müller, Andreas ; Prause, Felix ; Eck, Martin ; Goller, Jessica ; Milius, Wolfgang ; Breuning, Matthias:
The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions.
In: Chemistry : a European Journal.
Vol. 21
(2015)
Issue 35
.
- pp. 12488-12500.
ISSN 1521-3765
DOI: https://doi.org/10.1002/chem.201502090
Abstract in another language
The first modular and flexible synthesis of core-chiral bispidines was achieved by using an “inside-out” strategy. The key intermediate, a NBoc-activated bispidine lactam, was constructed in enantiomerically pure form from a chirally modified β-amino acid and 2-(acetoxymethyl)acrylonitrile in just five steps and good 48 % yield. A simple addition–reduction protocol permitted a highly endo-selective introduction of substituents and, thus, a fast and variable access to 2-endo-substituted and 2-endo,N-fused bi- and tricyclic bispidines. The new diamines were evaluated as the chiral ligands in asymmetric Henry reactions. Excellent enantioselectivities of up to 99 % ee and good diastereomeric ratios of up to 86:14 were reached with a copper(II) complex modified by a 2-endo,N-(3,3-dimethylpyrrolidine)-annelated bispidine. Its performance is superior to that of the well-known bispidines (−)-sparteine and the (+)-sparteine surrogate.
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: | Yes |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 11 Jan 2022 10:09 |
| Last Modified: | 11 Jan 2022 10:09 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68300 |