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- Title
Enantioselective Synthesis of Isoindolones via Palladium – Catalyzed Intramolecular Heck‐Mizoroki Reactions of Endocyclic Enamides Using N,N‐Ligands.
- Authors
Wiethan, Carson; Braga, Ingredy B.; Menezes da Silva, Vitor H.; Batista, João M.; Correia, Carlos Roque D.
- Abstract
The enantioselective synthesis of isoindolones via Heck‐Mizoroki reactions of endocyclic enamides using a palladium‐bis(oxazoline) catalyst system is described. The N,N‐ligands, which are under‐represented in palladium‐catalyzed reactions involving aryl halides, proved to be an effective and low‐cost alternative to their phosphine‐based chiral ligand counterparts. The intramolecular Heck reaction of aryl iodides and endocyclic enamides enabled the construction of tricyclic isoindolones containing tertiary and quaternary chiral centers under mild conditions in yields up to 73 % and enantiomeric ratios up to 97 : 3. Vibrational circular dichroism (VCD) was instrumental in determining the absolute configuration of the enantioenriched isoindolones.
- Subjects
VIBRATIONAL circular dichroism; PALLADIUM; HECK reaction; ARYL iodides; CHIRAL centers; PHOSPHINES
- Publication
ChemCatChem, 2023, Vol 15, Issue 12, p1
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.202300422