Synthesis of N -tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

Herein we report the zirconooxaziridine promoted aziridination of alkenes using chloramine T as the quantitative source of N. The reaction works with high yields, diastereoselectivities and stereospecificity for a wide variety of substituted alkenes. A potential mechanism involving the formation of...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 31; pp. 4909 - 4912
Main Authors Pinarci, Ali A, Daniecki, Noah, TenHoeve, Tyler M, Dellosso, Brandon, Madiu, Rufai, Mejia, Liliana, Bektas, Seda E, Moura-Letts, Gustavo
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 14.04.2022
Subjects
Alkenes
Catalysis
Molecular Structure
Substitutes
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Summary:Herein we report the zirconooxaziridine promoted aziridination of alkenes using chloramine T as the quantitative source of N. The reaction works with high yields, diastereoselectivities and stereospecificity for a wide variety of substituted alkenes. A potential mechanism involving the formation of a zirconooxaziridine complex as the active catalyst has been proposed and initial mechanistic data would indicate that a highly associative mechanism is the predominant pathway for this transformation.
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ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc00686c