Synthesis of Axially Chiral Biaryls via Enantioselective Ullmann Coupling of ortho-Chlorinated Aryl Aldehydes Enabled by a Chiral 2,2'-Bipyridine Ligand.
2,2′-Bipyridine Ligands
Asymmetric Catalysis
Biaryl Dials
Enantioselectivity
Reductive Homocoupling
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
21 11 2022
21 11 2022
Historique:
received:
17
08
2022
pubmed:
6
10
2022
medline:
16
11
2022
entrez:
5
10
2022
Statut:
ppublish
Résumé
The first nickel-catalyzed highly enantioselective reductive Ullmann coupling of ortho-chlorinated aryl aldehyde was achieved under mild reaction conditions with a chiral 2,2'-bipyridine ligand (+)-DTB-SBpy, thus providing axially chiral biphenyl or binaphthyl dials with up to 99 % yield and 99.5:0.5 er. The versatility of the products as common synthetic intermediates for diverse axially chiral ligands, catalysts, and functional molecules was demonstrated by short-step transformations. This protocol also allowed the concise and highly enantioselective formal total synthesis of biologically active natural products (+)-kotanin, (-)-isoschizandrin and (+)-gossypol.
Identifiants
pubmed: 36196003
doi: 10.1002/anie.202212108
doi:
Substances chimiques
Ligands
0
Aldehydes
0
2,2'-Dipyridyl
551W113ZEP
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202212108Informations de copyright
© 2022 Wiley-VCH GmbH.
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