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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.

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

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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