at Google ScholarTitle data
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.
Vol. 661
(2002)
Issue 1-2
.
- pp. 31-47.
ISSN 1872-8561
DOI: https://doi.org/10.1016/S0022-328X(02)01804-1
Abstract in another language
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.
Further data
| Item Type: | Article in a journal |
|---|---|
| Refereed: | Yes |
| Keywords: | Biaryls; Stereoselective synthesis; Atropisomers; Axial chirality; Ring opening; Dynamic kinetic resolution |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry III - Naturstoffsynthese und Katalyse > Professor Organic Chemistry III - Naturstoffsynthese und Katalyse - 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 III - Naturstoffsynthese und Katalyse |
| Result of work at the UBT: | No |
| DDC Subjects: | 500 Science > 540 Chemistry |
| Date Deposited: | 12 Jan 2022 10:08 |
| Last Modified: | 02 Mar 2026 08:44 |
| URI: | https://eref.uni-bayreuth.de/id/eprint/68336 |