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Photoredox approach to N-Acyl-N'-aryl-N,N'-aminals using enamides and their conversion to γ-lactams

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journal contribution
posted on 2018-02-09, 11:43 authored by Olusesan K. Koleoso, Mark ElsegoodMark Elsegood, Simon J. Teat, Marc KimberMarc Kimber
A photoredox catalytic approach to synthetically valuable N-acyl-N'-aryl-N,N'-aminals is described. This method uses the addition of a radical precursor to enamides, with subsequent interception of the cationic iminium intermediate with an arylamine. The reaction has been shown to be compatible with electron-rich and electron-deficient arylamines, and moderate to good levels of diastereoselectivity can be attained using a chiral enamide. Furthermore, the N-acyl-N'-aryl-N,N'-aminal reaction products can be readily cyclized, providing a novel synthetic route to valuable γ-lactams.

Funding

We gratefully acknowledge financial support from Loughborough University and the Tertiary Education Trust Fund (TETFund) Abuja, Nigeria (O.K.K.). We acknowledge support of the EPSRC via grant EP/M027341/1.,We gratefully acknowledge financial support from Loughborough University and the Tertiary Education Trust Fund (TETFund) Abuja, Nigeria (OKK). We thank Dr. Mark Edgar (Loughborough) for NMR structure determination; the Advanced Light Source is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231; and the support of the EPSRC via grant EP/M027341/1.

History

School

  • Science

Department

  • Chemistry

Published in

Organic Letters

Citation

KOLEOSO, O.K. ... et al, 2018. Photoredox approach to N-Acyl-N'-aryl-N,N'-aminals using enamides and their conversion to γ-lactams. Organic Letters, 20 (4), pp.1003–1006.

Publisher

© American Chemical Society

Version

  • AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) licence. Full details of this licence are available at: http://creativecommons.org/licenses/by-nc/4.0/

Acceptance date

2018-01-26

Publication date

2018-01-26

Notes

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.7b03946.

DOI

ISSN

1523-7052

eISSN

1523-7052

Publisher version

Language

  • en

Location

United States

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    Loughborough Publications

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    untaggedChemical Sciences not elsewhere classified

    Licence

    CC BY-NC 4.0

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