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The lactone concept : a novel approach to the metal-assisted atroposelective construction of axially chiral biaryl systems

Titelangaben

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 CO 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