Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

Joshua Farndon; Tom Young; John Bower

doi:10.1021/jacs.8b10485

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

Joshua Farndon, Tom Young, John Bower

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Abstract

In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

Original language	English
Pages (from-to)	17846-17850
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	140
Issue number	51
Early online date	13 Dec 2018
DOIs	https://doi.org/10.1021/jacs.8b10485
Publication status	Published - 26 Dec 2018

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at https://pubs.acs.org/doi/10.1021/jacs.8b10485 . Please refer to any applicable terms of use of the publisher.
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title = "Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction",

abstract = "In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.",

author = "Joshua Farndon and Tom Young and John Bower",

year = "2018",

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doi = "10.1021/jacs.8b10485",

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TY - JOUR

T1 - Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent

T2 - An Aza-Prilezhaev Reaction

AU - Farndon, Joshua

AU - Young, Tom

AU - Bower, John

PY - 2018/12/26

Y1 - 2018/12/26

N2 - In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

AB - In situ deprotection (TFA) of O-Ts activated N-Boc hydroxylamines triggers intramolecular aziridination of N-tethered alkenes to provide complex N-heterocyclic ring systems. Synthetic and computational studies corroborate a diastereospecific aza-Prilezhaev-type mechanism. The feasibility of related intermolecular alkene aziridinations is also demonstrated.

U2 - 10.1021/jacs.8b10485

DO - 10.1021/jacs.8b10485

M3 - Article (Academic Journal)

C2 - 30543287

SN - 0002-7863

VL - 140

SP - 17846

EP - 17850

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 51

ER -

Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction

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