Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

Ali A. Pinarci; Noah Daniecki; Tyler M. TenHoeve; Brandon Dellosso; Rufai Madiu; Liliana Mejia; Seda E. Bektas; Gustavo Moura-Letts

doi:10.1039/d2cc00686c

Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

Ali A. Pinarci, Noah Daniecki, Tyler M. TenHoeve, Brandon Dellosso, Rufai Madiu, Liliana Mejia, Seda E. Bektas, Gustavo Moura-Letts

Chemistry

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	4909-4912
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	31
DOIs	https://doi.org/10.1039/d2cc00686c
State	Published - Mar 21 2022

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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title = "Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis",

abstract = "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.",

author = "Pinarci, {Ali A.} and Noah Daniecki and TenHoeve, {Tyler M.} and Brandon Dellosso and Rufai Madiu and Liliana Mejia and Bektas, {Seda E.} and Gustavo Moura-Letts",

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year = "2022",

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doi = "10.1039/d2cc00686c",

language = "English (US)",

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T1 - Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

AU - Pinarci, Ali A.

AU - Daniecki, Noah

AU - TenHoeve, Tyler M.

AU - Dellosso, Brandon

AU - Madiu, Rufai

AU - Mejia, Liliana

AU - Bektas, Seda E.

AU - Moura-Letts, Gustavo

PY - 2022/3/21

Y1 - 2022/3/21

N2 - 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.

AB - 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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DO - 10.1039/d2cc00686c

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AN - SCOPUS:85128488536

SN - 1359-7345

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EP - 4912

JO - Chemical Communications

JF - Chemical Communications

IS - 31

ER -

Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

Abstract

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