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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.

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

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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