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Atropo-Diastereoselective Cleavage of Configurationally Unstable Biaryl Lactones with Alkali Metal Activated Primary 1-Arylethylamines

Title data

Bringmann, Gerhard ; Breuning, Matthias ; Tasler, Stefan ; Endress, Heike ; Ewers, Christian L. J. ; Göbel, Lothar ; Peters, Karl ; Peters, Eva-Maria:
Atropo-Diastereoselective Cleavage of Configurationally Unstable Biaryl Lactones with Alkali Metal Activated Primary 1-Arylethylamines.
In: Chemistry : a European Journal. Vol. 5 (1999) Issue 10 . - pp. 3029-3038.
ISSN 1521-3765
DOI: https://doi.org/10.1002/(SICI)1521-3765(19991001)5:10<3029::AID-CHEM3029>3.0.CO;2-5

Abstract in another language

Axially chiral biaryls with diastereomeric ratios of up to 95:5 are synthesized by highly atropo-selective cleavage of configurationally unstable, lactone-bridged biaryls with chiral metalated 1-arylethlamines (see scheme). This methodology permits optional preparation of each of the two atropisomers from the same lactone precursor just by the use of the appropiate amine reagent or its enantiomer for the ring-opening (atropo-divergence), and offers the possibility of recycling the minor isomer back to the lactone. The chiral 1-arylethyl(amine) group can subsequently split off without any loss of stereoinformation at the axis.

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: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 12 Jan 2022 13:19
Last Modified: 12 Jan 2022 13:19
URI: https://eref.uni-bayreuth.de/id/eprint/68343