Nickel-Catalyzed Enantioselective C(sp3)-C(sp3) Cross-Electrophile Coupling of N-Sulfonyl Styrenyl Aziridines with Alkyl Bromides.
J Am Chem Soc
; 146(37): 25426-25432, 2024 Sep 18.
Article
em En
| MEDLINE
| ID: mdl-39231321
ABSTRACT
Herein, we report the first example of a highly enantioselective alkylative aziridine ring opening. Under the catalysis of a chiral nickel/pyridine-imidazoline complex, asymmetric C(sp3)-C(sp3) cross-electrophile coupling between racemic N-sulfonyl styrenyl aziridines and readily available primary alkyl bromides furnishes a variety of highly enantioenriched phenethylamine derivatives with complete regiocontrol and good functional group tolerance. Preliminary mechanistic studies support a reaction pathway consisting of regioselective iodolysis of aziridines in situ and subsequent enantioconvergent coupling of the generated ß-amino benzyl iodides with alkyl bromides.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2024
Tipo de documento:
Article