FAM-Ag-catalyzed asymmetric synthesis of heteroaryl-substituted pyrrolidines.
asymmetric synthesis
chiral FAM ligands
chiral metal catalyst
heteroaryl-substituted pyrrolidines
Journal
Chirality
ISSN: 1520-636X
Titre abrégé: Chirality
Pays: United States
ID NLM: 8914261
Informations de publication
Date de publication:
08 2021
08 2021
Historique:
revised:
20
04
2021
received:
24
02
2021
accepted:
28
04
2021
pubmed:
27
5
2021
medline:
27
5
2021
entrez:
26
5
2021
Statut:
ppublish
Résumé
New derivatives of FAM (ferrocenyl aziridinyl methanol) ligands NFAM1-4 (naphthyl ferrocenyl aziridinyl methanol) and CFAM1-4 (cyclohexyl ferrocenyl aziridinyl methanol) were synthesized to form a small ligand library and used as chiral catalysts with AgOAc for the asymmetric synthesis of heteroaryl-substituted pyrrolidines by the 1,3-dipolar cycloaddition (1,3-DC) reaction of azomethine ylides. 2-Thienyl, 2-furyl, 2-, 3-, and 4-pyridyl aldimines were prepared and used with N-methylmaleimide, dimethyl maleate, tert-butyl acrylate, methyl acrylate, and acrylonitrile to form the corresponding heteroaryl-substituted pyrrolidines. 1,3-DC reactions yielded the expected cycloadducts in up to 89% yield and up to 76% ee that could be increased up to 95% ee upon crystallization. New chiral ligands NFAM1-4 and CFAM1-4 were fully characterized, and their absolute stereochemistry was determined by single-crystal X-ray analysis.
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
465-478Subventions
Organisme : Middle East Technical University
Organisme : Scientific and Technological Research Council of Turkey
ID : 118Z414
Informations de copyright
© 2021 Wiley Periodicals LLC.
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