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Synthesis of N-Tosyl Allylic Amines from Substituted Alkenes via Vanadoxaziridine Catalysis.
Madiu, Rufai; Doran, Erin L; Doran, Jenna M; Pinarci, Ali A; Dhillon, Kiran; Rivera, Dominic A; Howard, Amari M; Stroud, James L; Moskovitz, Dylan A; Finneran, Steven J; Singer, Alyssa N; Rossi, Morgan E; Moura-Letts, Gustavo.
Afiliación
  • Madiu R; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Doran EL; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Doran JM; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Pinarci AA; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Dhillon K; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Rivera DA; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Howard AM; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Stroud JL; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Moskovitz DA; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Finneran SJ; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Singer AN; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Rossi ME; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
  • Moura-Letts G; Department of Chemistry and Biochemistry, Rowan University, 201 Mullica Hill Rd., Glassboro, New Jersey 08028, United States.
J Org Chem ; 89(6): 4001-4008, 2024 Mar 15.
Article en En | MEDLINE | 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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Texto completo: 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
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 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