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Bringmann, Gerhard ; Breuning, Matthias ; Pfeifer, Robert-M. ; Schenk, Wolfdieter A. ; Kamikawa, Ken ; Uemura, Motokazu:
The lactone concept : a novel approach to the metal-assisted atroposelective construction of axially chiral biaryl systems.
In: Journal of Organometallic Chemistry.
Bd. 661
(2002)
Heft 1-2
.
- S. 31-47.
ISSN 0022-328X
DOI: https://doi.org/10.1016/S0022-328X(02)01804-1
Abstract
The atroposelective synthesis of axially chiral biaryls via configurationally unstable, lactone-bridged biaryls is reviewed. These key molecules are easily accessible by regioselective intramolecular cross-coupling of ester-linked, even sterically hindered aromatic portions and can be cleaved highly atropo-enantio- or -diastereoselectively by three principal options, either (a) by using a wide range of chiral metalated nucleophiles (usually with external asymmetric induction), (b) after Lewis acid activation of the lactone CO function using uncharged chiral or achiral nucleophiles, or (c) with internal asymmetric induction, using the stereoelement of planar chirality originating from η6-coordination (typically involving Cr or Ru complexes). The resulting ring-opened configurationally stable biaryls are obtained in mostly excellent chemical and optical yields. By the choice of the respective enantiomer of the nucleophile, the method allows the atropo-divergent synthesis of both atropisomers from the same immediate biaryl precursor and, if required, a recycling of the undesired minor atropisomer is possible, too. Such advantages are otherwise well-known for the stereoselective preparation of centrochiral compounds.
Weitere Angaben
| Publikationsform: | Artikel in einer Zeitschrift |
|---|---|
| Begutachteter Beitrag: | Ja |
| Keywords: | Biaryls; Stereoselective synthesis; Atropisomers; Axial chirality; Ring opening; Dynamic kinetic resolution |
| 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: | Nein |
| Themengebiete aus DDC: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
| Eingestellt am: | 12 Jan 2022 10:08 |
| Letzte Änderung: | 12 Jan 2022 10:08 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68336 |