Chiral Brønsted acid-catalyzed asymmetric synthesis of N-aryl-cis-aziridine carboxylate esters

Sean P. Bew; John Liddle; David L. Hughes; Paolo Pesce; Sean M. Thurston

doi:10.1002/anie.201611990

Chiral Brønsted acid-catalyzed asymmetric synthesis of N-aryl-cis-aziridine carboxylate esters

Sean P. Bew, John Liddle, David L. Hughes, Paolo Pesce, Sean M. Thurston

Synthetic and Medicinal Chemistry

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

32 Citations (Scopus)

28 Downloads (Pure)

Abstract

We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.

Original language	English
Pages (from-to)	5322–5326
Number of pages	5
Journal	Angewandte Chemie-International Edition
Volume	56
Issue number	19
Early online date	5 Apr 2017
DOIs	https://doi.org/10.1002/anie.201611990
Publication status	Published - 2 May 2017

Keywords

Asymmetrische Katalyse
Aziridine
Brønsted-Säuren
Mehrkomponentenreaktionen

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10.1002/anie.201611990Licence: CC BY

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This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 991 KBLicence: CC BY

http://onlinelibrary.wiley.com/doi/10.1002/anie.201611990/abstractLicence: CC BY

Sean Bew
- S.Bewuea.acuk
- School of Chemistry, Pharmacy and Pharmacology - Associate Professor in Chemistry
- Synthetic and Medicinal Chemistry - Member
Person: Research Group Member, Academic, Teaching and Research

Cite this

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title = "Chiral Br{\o}nsted acid-catalyzed asymmetric synthesis of N-aryl-cis-aziridine carboxylate esters",

abstract = "We report a multi-component asymmetric Br{\o}nsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.",

keywords = "Asymmetrische Katalyse, Aziridine, Br{\o}nsted-S{\"a}uren, Mehrkomponentenreaktionen",

author = "Bew, {Sean P.} and John Liddle and Hughes, {David L.} and Paolo Pesce and Thurston, {Sean M.}",

year = "2017",

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doi = "10.1002/anie.201611990",

language = "English",

volume = "56",

pages = "5322–5326",

journal = "Angewandte Chemie-International Edition",

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TY - JOUR

T1 - Chiral Brønsted acid-catalyzed asymmetric synthesis of N-aryl-cis-aziridine carboxylate esters

AU - Bew, Sean P.

AU - Liddle, John

AU - Hughes, David L.

AU - Pesce, Paolo

AU - Thurston, Sean M.

PY - 2017/5/2

Y1 - 2017/5/2

N2 - We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.

AB - We report a multi-component asymmetric Brønsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.

KW - Asymmetrische Katalyse

KW - Aziridine

KW - Brønsted-Säuren

KW - Mehrkomponentenreaktionen

U2 - 10.1002/anie.201611990

DO - 10.1002/anie.201611990

M3 - Article

SN - 1433-7851

VL - 56

SP - 5322

EP - 5326

JO - Angewandte Chemie-International Edition

JF - Angewandte Chemie-International Edition

IS - 19

ER -

Chiral Brønsted acid-catalyzed asymmetric synthesis of N-aryl-cis-aziridine carboxylate esters

Abstract

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Sean Bew

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