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Synthesis of N-Tosyl Allylic Amines from Substituted Alkenes via Vanadoxaziridine Catalysis.


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.

SUBMITTER: Madiu R 

PROVIDER: S-EPMC10949238 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Synthesis of <i>N</i>-Tosyl Allylic Amines from Substituted Alkenes via Vanadoxaziridine Catalysis.

Madiu Rufai R   Doran Erin L EL   Doran Jenna M JM   Pinarci Ali A AA   Dhillon Kiran K   Rivera Dominic A DA   Howard Amari M AM   Stroud James L JL   Moskovitz Dylan A DA   Finneran Steven J SJ   Singer Alyssa N AN   Rossi Morgan E ME   Moura-Letts Gustavo G  

The Journal of organic chemistry 20240226 6


Herein, we report the catalytic allylic amination of α-methylalkenes with V<sub>2</sub>O<sub>3</sub>Dipic<sub>2</sub>(HMPA)<sub>2</sub> and chloramine T as the quantitative source of <i>N</i>. The reaction works with high yields and stereoselectivities for α-methylalkenes. A proposed tosylnitrene-free catalytic cycle involving the formation of vanadoxaziridine complex <b>1</b> as the active catalyst and aminovanadation across the substrate as the rate-determining step has been proposed. Initial  ...[more]

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