Synthesis of N-Tosyl Allylic Amines from Substituted Alkenes via Vanadoxaziridine Catalysis.
J Org Chem
; 89(6): 4001-4008, 2024 Mar 15.
Article
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| ID: mdl-38407036
ABSTRACT
Herein, we report the catalytic allylic amination of α-methylalkenes with V2O3Dipic2(HMPA)2 and chloramine T as the quantitative source of N. The reaction works with high yields and stereoselectivities for α-methylalkenes. A proposed tosylnitrene-free catalytic cycle involving the formation of vanadoxaziridine complex 1 as the active catalyst and aminovanadation across the substrate as the rate-determining step has been proposed. Initial kinetic and competition experiments provide evidence for the proposed mechanism.
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1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2024
Tipo del documento:
Article
País de afiliación:
Estados Unidos
Pais de publicación:
Estados Unidos