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The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the "lactone methodology"

Title data

Bringmann, Gerhard ; Tasler, Stefan ; Pfeifer, Robert-M. ; Breuning, Matthias:
The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the "lactone methodology".
In: Journal of Organometallic Chemistry. Vol. 661 (2002) Issue 1-2 . - pp. 49-65.
ISSN 1872-8561
DOI: https://doi.org/10.1016/S0022-328X(02)01819-3

Abstract in another language

Axially chiral biaryls have become increasingly important during the past years—as structurally, biosynthetically, and pharmacologically remarkable natural products, but also as useful tools in asymmetric synthesis: as chiral reagents, ligands, and catalysts. Nevertheless, only few generally applicable synthetic protocols for the atropo-enantio- or -diastereoselective construction of biaryl bonds have been developed. The ‘lactone methodology’ as described in detail in the preceeding article, provides directed, atropo-divergent access to any of the two respective atropisomers starting from the identical immediate precursor, a (usually) configurationally unstable, since lactone-bridged biaryl. In this article the efficiency of the ‘lactone method’ in the total synthesis of natural products and in the preparation of axially chiral ligands is demonstrated for selected examples.

Further data

Item Type: Article in a journal
Refereed: Yes
Keywords: Biaryl axis; Asymmetric synthesis; Natural products; Biaryl ligands; Axial chirality; Enantioselective catalysis
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 09:59
Last Modified: 02 Mar 2026 08:43
URI: https://eref.uni-bayreuth.de/id/eprint/68335