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CatHet SIGNED

New Catalytic Asymmetric Strategies for N-Heterocycle Synthesis

Total Cost €

0

EC-Contrib. €

0

Partnership

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 CatHet project word cloud

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

synthetically    intermediates    candidate    surprisingly    organic    total    decades    goals    generalise    synthesis    urgent    points    decreased    syntheses    60    transformative    generation    actually    1990s    starting    variety    chemistry    realisation    organometallic    exert    acceleration    classes    drug    intermediate    catalysis    efficient    consequently    notable    amenable    preliminary    progression    metal    absolute    marketed    scaffolds    heteroannulation    stereochemistry    outline    operationally    asymmetric    time    stage    medicinal    enantiomers    philosophy    compounds    tremendous    insertion    world    selling    heterocyclic    divergence    compelling    transcend    marketplace    natural    despite    sigma    small    libraries    single    flexible    privileged    complexity    diverse    manifolds    discovery    drugs    catalytic    mid    trapping    holds    chiral    platforms    made    aspirational    unusual    correlation    bonds    relative    transition    applicability    approximately    80    molecule    mentioned   

Project "CatHet" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITY OF BRISTOL 

Organization address
address: BEACON HOUSE QUEENS ROAD
city: BRISTOL
postcode: BS8 1QU
website: www.bristol.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]
 Project website https://bowerresearchgroup.wordpress.com/
 Total cost 1˙548˙738 €
 EC max contribution 1˙548˙738 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2014-STG
 Funding Scheme ERC-STG
 Starting year 2015
 Duration (year-month-day) from 2015-04-01   to  2020-03-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 1˙548˙738.00

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 Project objective

Medicinal chemistry requires more efficient and diverse methods for the asymmetric synthesis of chiral scaffolds. Over 60% of the world’s top selling small molecule drug compounds are chiral and, of these, approximately 80% are marketed as single enantiomers. There is a compelling correlation between drug candidate “chiral complexity” and the likelihood of progression to the marketplace. Surprisingly, and despite the tremendous advances made in catalysis over the past several decades, the “chiral complexity” of drug discovery libraries has actually decreased, while, at the same time, for the reasons mentioned above, the “chiral complexity” of marketed drugs has increased. Since the mid-1990s, there has been a notable acceleration of this “complexity divergence”. Consequently, there is now an urgent need to provide efficient processes that directly access privileged chiral scaffolds. It is our philosophy that catalysis holds the key here and new processes should be based upon platforms that can exert control over both absolute and relative stereochemistry. In this proposal we outline the development of a range of N-heteroannulation processes based upon the catalytic generation and trapping of unique or unusual classes of organometallic intermediate derived from transition metal insertion into C-C and C-N sigma-bonds. We will provide a variety of enabling methodologies and demonstrate applicability in flexible total syntheses of important natural product scaffolds. The processes proposed are synthetically flexible, operationally simple and amenable to asymmetric catalysis. Likely starting points, based upon preliminary results, will set the stage for the realisation of aspirational and transformative goals. Through the study of the organometallic intermediates involved here, there is potential to generalise these new catalytic manifolds, such that this research will transcend N heterocyclic chemistry to provide enabling methods for organic chemistry as a whole.

 Publications

year authors and title journal last update
List of publications.
2018 Ian R. Hazelden, Rafaela C. Carmona, Thomas Langer, Paul G. Pringle, and John F. Bower
Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201801109
Angewandte Chemie International Edition 2019-10-17
2018 Joshua J. Farndon, Tom A. Young, John F. Bower
Stereospecific Alkene Aziridination Using a Bifunctional Amino-Reagent: An Aza-Prilezhaev Reaction
published pages: 17846-17850, ISSN: 0002-7863, DOI: 10.1021/jacs.8b10485
Journal of the American Chemical Society 140/51 2019-10-17
2018 Andrew G. Dalling, John F. Bower
Synthesis of Nitrogen Heterocycles via Directed Carbonylative C–C Bond Activation of Cyclopropanes
published pages: 595-600, ISSN: 0009-4293, DOI: 10.2533/chimia.2018.595
CHIMIA International Journal for Chemistry 72/9 2019-10-17
2019 Xiaofeng Ma, Ian R. Hazelden, Thomas Langer, Rachel H. Munday, John F. Bower
Enantioselective Aza-Heck Cyclizations of N -(Tosyloxy)carbamates: Synthesis of Pyrrolidines and Piperidines
published pages: 3356-3360, ISSN: 0002-7863, DOI: 10.1021/jacs.8b12689
Journal of the American Chemical Society 141/8 2019-10-17
2019 Olivia Boyd, Gangwei Wang, Olga Sokolova, Adam Calow, Sophie Bertrand, John Bower
Modular Access to Eight-Membered N-Heterocycles by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201910276
Angewandte Chemie International Edition 2019-10-17
2018 Simon Grélaud, Phillippa Cooper, Lyman J. Feron, John F. Bower
Branch-Selective and Enantioselective Iridium-Catalyzed Alkene Hydroarylation via Anilide-Directed C–H Oxidative Addition
published pages: 9351-9356, ISSN: 0002-7863, DOI: 10.1021/jacs.8b04627
Journal of the American Chemical Society 140/30 2019-10-17
2018 Gang-Wei Wang, John F. Bower
Modular Access to Azepines by Directed Carbonylative C–C Bond Activation of Aminocyclopropanes
published pages: 2743-2747, ISSN: 0002-7863, DOI: 10.1021/jacs.7b13087
Journal of the American Chemical Society 140/8 2019-10-17
2019 Andrew G. Dalling, Takayuki Yamauchi, Niall G. McCreanor, Lydia Cox, John F. Bower
Carbonylative C−C Bond Activation of Electron-Poor Cyclopropanes: Rhodium-Catalyzed (3+1+2) Cycloadditions of Cyclopropylamides
published pages: 221-225, ISSN: 1433-7851, DOI: 10.1002/anie.201811460
Angewandte Chemie International Edition 58/1 2019-10-17
2017 Gabriele Fumagalli, Steven Stanton, and John F. Bower
Recent Methodologies That Exploit C−C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes
published pages: , ISSN: 0009-2665, DOI: 10.1021/acs.chemrev.6b00599
Chemical Reviews 2019-10-17
2017 Nicholas J. Race, Adele Faulkner, Gabriele Fumagalli, Takayuki Yamauchi, James S. Scott, Marie Rydén-Landergren, Hazel A. Sparkes, John F. Bower
Enantioselective Narasaka–Heck cyclizations: synthesis of tetrasubstituted nitrogen-bearing stereocenters
published pages: 1981-1985, ISSN: 2041-6520, DOI: 10.1039/c6sc04466b
Chem. Sci. 8/3 2019-05-29
2017 Xiaofeng Ma, Joshua J. Farndon, Tom A. Young, Natalie Fey, John F. Bower
A Simple and Broadly Applicable C−N Bond Forming Dearomatization Protocol Enabled by Bifunctional Amino Reagents
published pages: 14531-14535, ISSN: 1433-7851, DOI: 10.1002/anie.201708176
Angewandte Chemie International Edition 56/46 2019-05-29
2017 Craig S. Buxton, David C. Blakemore, John F. Bower
Reductive Coupling of Acrylates with Ketones and Ketimines by a Nickel-Catalyzed Transfer-Hydrogenative Strategy
published pages: 13824-13828, ISSN: 1433-7851, DOI: 10.1002/anie.201707531
Angewandte Chemie International Edition 56/44 2019-05-29
2016 Megan H. Shaw, John F. Bower
Synthesis and applications of rhodacyclopentanones derived from C–C bond activation
published pages: 10817-10829, ISSN: 1359-7345, DOI: 10.1039/C6CC04359C
Chem. Commun. 52/72 2019-05-29
2016 Gang-Wei Wang, Niall G. McCreanor, Megan H. Shaw, William G. Whittingham, John F. Bower
New Initiation Modes for Directed Carbonylative C–C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes
published pages: , ISSN: 0002-7863, DOI: 10.1021/jacs.6b08608
Journal of the American Chemical Society 2019-05-29
2016 Ian R. Hazelden, Xiaofeng Ma, Thomas Langer, John F. Bower
Diverse N -Heterocyclic Ring Systems via Aza-Heck Cyclizations of N -(Pentafluorobenzoyloxy)sulfonamides
published pages: 11198-11202, ISSN: 1433-7851, DOI: 10.1002/anie.201605152
Angewandte Chemie International Edition 55/37 2019-05-29
2015 Megan H. Shaw, Rosemary A. Croft, William G. Whittingham, John F. Bower
Modular Access to Substituted Azocanes via a Rhodium-Catalyzed Cycloaddition–Fragmentation Strategy
published pages: 8054-8057, ISSN: 0002-7863, DOI: 10.1021/jacs.5b05215
Journal of the American Chemical Society 137/25 2019-05-29
2016 Niall G. McCreanor, Steven Stanton, John F. Bower
Capture–Collapse Heterocyclization: 1,3-Diazepanes by C–N Reductive Elimination from Rhodacyclopentanones
published pages: 11465-11468, ISSN: 0002-7863, DOI: 10.1021/jacs.6b07046
Journal of the American Chemical Society 138/36 2019-05-29
2017 Joshua J. Farndon, Xiaofeng Ma, John F. Bower
Transition Metal Free C–N Bond Forming Dearomatizations and Aryl C–H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent
published pages: 14005-14008, ISSN: 0002-7863, DOI: 10.1021/jacs.7b07830
Journal of the American Chemical Society 139/40 2019-05-29

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