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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.
Bd. 21
(2015)
Heft 35
.
- S. 12488-12500.
ISSN 1521-3765
DOI: https://doi.org/10.1002/chem.201502090
Abstract
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.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Institutionen der Universität: | Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Professur Organische Chemie > Professur Organische Chemie - Univ.-Prof. Dr. Matthias Breuning Fakultäten Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie Fakultäten > Fakultät für Biologie, Chemie und Geowissenschaften > Fachgruppe Chemie > Professur Organische Chemie |
| Titel an der UBT entstanden: | Ja |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 11 Jan 2022 10:09 |
| Letzte Änderung: | 11 Jan 2022 10:09 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68300 |