Catalytic Atropenantioselective Heteroannulation between Isocyanoacetates and Alkynyl Ketones: Synthesis of Enantioenriched Axially Chiral 3-Arylpyrroles.
arylpyrrole
asymmetric synthesis
axial chirality
homogeneous catalysis
isocyanide
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:
28 Jan 2019
28 Jan 2019
Historique:
received:
04
11
2018
pubmed:
28
11
2018
medline:
28
11
2018
entrez:
28
11
2018
Statut:
ppublish
Résumé
We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of α-isocyanoacetates with β-aryl-α,β-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkaloid occurred chemoselectively to afford enantioenriched 3-arylpyrroles in high yields with excellent enantiomeric excesses. The pyrrole ring was constructed de novo in this process.
Identifiants
pubmed: 30480863
doi: 10.1002/anie.201812654
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1494-1498Subventions
Organisme : Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
ID : N° 20021-178846/1
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.