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PHOTOCAMSYN SIGNED

Photocatalytic Reductive Coupling of Imines: A New Platform for Chiral Amine Synthesis

Total Cost €

0

EC-Contrib. €

0

Partnership

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 PHOTOCAMSYN project word cloud

Explore the words cloud of the PHOTOCAMSYN project. It provides you a very rough idea of what is the project "PHOTOCAMSYN" about.

biologically    alkynes    intermediates    stabilise    powerful    nucleophilic    natural    catalytic    careful    turn    synthesis    branched    nucleophiles    electrophilic    undergoing    accordingly    amine    chemistry    accessed    anionic    offers    plan    dominate    umpolung    organometallic    synthetically    imines    applicable    date       synthetic    agrochemicals    led    reactions    takes    reactivity    amino    species    free    perspectives    reagents    forming    centered    alkenes    polarity    commonplace    derivatives    broad    motifs    suites    direct    react    academic    alpha    generate    bond    generation    pharmaceuticals    modes    hydrogen    amines    possibility    industrial    untapped    reverse    advantage    chiral    deprotonation    formal    precursors    whilst    electron    substrates    reversal    reductive    broadly    radical    asymmetric    functionalisation    strategy    limited    versions    carbon    atom    rendering    wealth    imine    pi    photochemical   

Project "PHOTOCAMSYN" data sheet

The following table provides information about the project.

Coordinator
THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD 

Organization address
address: WELLINGTON SQUARE UNIVERSITY OFFICES
city: OXFORD
postcode: OX1 2JD
website: www.ox.ac.uk

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country United Kingdom [UK]
 Total cost 183˙454 €
 EC max contribution 183˙454 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2017
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2018
 Duration (year-month-day) from 2018-06-21   to  2020-06-20

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD UK (OXFORD) coordinator 183˙454.00

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 Project objective

Chiral α-branched amines and their derivatives are commonplace in pharmaceuticals, agrochemicals and biologically relevant natural products. Accordingly, the development of new synthetically powerful methods for their synthesis, and/or further functionalisation, through new carbon-carbon bond forming processes is both important and timely from academic and industrial perspectives. Such chiral α-branched amine motifs can be accessed from electrophilic imine substrates, through direct addition of carbon-centered nucleophiles such as organometallic reagents and electron rich π-nucleophiles. This traditional approach takes advantage of the easy formation of imines and their natural polarity and has led to numerous developments over the years. Whilst nucleophilic addition reactions dominate the chemistry of imines, polarity reversal is possible but requires the careful design of imine precursors able to stabilise anionic intermediates following deprotonation. Free radical chemistry offers the possibility to reverse the polarity of imine derivatives; the formal addition of a hydrogen atom to the C=N π-bond can generate a nucleophilic α-amino radical able to react with alkenes and alkynes. However, to date these approaches have been limited by the way the radical is generated. Here we propose a new and broadly applicable ‘umpolung’ approach to access chiral α-branched amine motifs directly from imine substrates. Our plan is to design and develop a new reductive photochemical system that will allow the direct generation of ‘free’ nucleophilic α-amino radical species capable of undergoing a broad range of synthetically useful carbon-carbon bond forming processes. This non-classical umpolung strategy has a wealth of untapped synthetic potential and will allow the development of new modes of reactivity each in turn rendering new suites of synthetic methodologies including catalytic asymmetric versions.

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