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GAINBYSTRAIN SIGNED

Gain by Strain: Precise Cuts of Cyclopropanes as Key to Molecular Complexity

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 GAINBYSTRAIN project word cloud

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Project "GAINBYSTRAIN" data sheet

The following table provides information about the project.

Coordinator
TECHNISCHE UNIVERSITAET BRAUNSCHWEIG 

Organization address
address: UNIVERSITAETSPLATZ 2
city: BRAUNSCHWEIG
postcode: 38106
website: www.tu-braunschweig.de

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 Germany [DE]
 Project website http://www.werzlab.de
 Total cost 1˙994˙250 €
 EC max contribution 1˙994˙250 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2014-CoG
 Funding Scheme ERC-COG
 Starting year 2015
 Duration (year-month-day) from 2015-07-01   to  2021-06-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    TECHNISCHE UNIVERSITAET BRAUNSCHWEIG DE (BRAUNSCHWEIG) coordinator 1˙994˙250.00

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 Project objective

A central discipline of chemistry is the design und creation of molecules with defined structural and chemical properties. Stretching synthetic horizons is a never-ending endeavor to inspirit the chemist’ s creativity in preparing compounds and materials yet to be discovered. Relying on their high strain energy cyclopropanes, as carriers of the most fundamental ring geometry, offer a unique reactivity which allows for a multitude of transformations being grouped in ring-opening reactions, cycloadditions and rearrangements. Major advantage of all these processes is the cyclopropane-derived intrinsic atom-economy. In this research project, we propose a number of uncommon and challenging reactions making use of donor-acceptor cyclopropanes. Introducing a distinctively controlled bond cleavage we seek to develop novel modes of 1,3-bifunctionalization by σ-bond metathesis, by using hypervalent iodine reagents and by merging organocatalysis with photoredox catalysis. Unprecedented ring-enlargements to four-membered rings by [31]-cycloadditions employing isonitriles, carbenes and nitrenes are envisioned, aryne insertions into the three-membered ring leading to indane systems are planned and a general concept for [33]-cycloadditions with 1,3-dipoles is presented paving the way to unusual syntheses of heterocycles. A distinct class of compounds obtainable by our methodology will set the stage to access completely unexplored heterocyclic π-systems being of interest for material science and molecular electronics. Besides our central goals of advancing organic methodology and to demonstrating the synthetic utility of these novel reactions, we anticipate that mechanistic insights gained by experimental and computational means will be of high impact for the chemistry of this fundamental structural unit in general.

 Publications

year authors and title journal last update
List of publications.
2019 Alexander Lücht, Peter G. Jones, Daniel B. Werz
Reactions of 3,3′-Linked Bispyrroles with Carbon Electrophiles
published pages: 5254-5260, ISSN: 1434-193X, DOI: 10.1002/ejoc.201900106
European Journal of Organic Chemistry 2019/31-32 2020-03-05
2019 Martin Petzold, Peter G. Jones, Daniel B. Werz
(3+3)-Annulation of Carbonyl Ylides with Donor-Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis
published pages: 6225-6229, ISSN: 1433-7851, DOI: 10.1002/anie.201814409
Angewandte Chemie International Edition 58/19 2020-03-05
2018 André U. Augustin, Marius Busse, Peter G. Jones, Daniel B. Werz
Formal Insertion of Thioketenes into Donor–Acceptor Cyclopropanes by Lewis Acid Catalysis
published pages: 820-823, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b03961
Organic Letters 20/3 2020-03-05
2019 Alexander Kreft, Alexander Lücht, Jörg Grunenberg, Peter G. Jones, Daniel B. Werz
Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity
published pages: 1955-1959, ISSN: 1433-7851, DOI: 10.1002/anie.201812880
Angewandte Chemie International Edition 58/7 2020-03-05
2019 André U. Augustin, Peter G. Jones, Daniel B. Werz
Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
published pages: 11620-11624, ISSN: 0947-6539, DOI: 10.1002/chem.201902160
Chemistry – A European Journal 25/50 2020-02-28
2019 André U. Augustin, J. Luca Merz, Peter G. Jones, Grzegorz Mlostoń, and Daniel B. Werz
(4+3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines
published pages: , ISSN: , DOI:
2020-02-28
2020 Daniel B. Werz, Akkattu T. Biju
Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes
published pages: 3385-3398, ISSN: 1433-7851, DOI: 10.1002/anie.201909213
Angewandte Chemie International Edition 59/9 2020-02-28
2017 André U. Augustin, Maximilian Sensse, Peter G. Jones, Daniel B. Werz
Stereospecific Reactions of Donor-Acceptor Cyclopropanes with Thioketones: Access to Highly Substituted Tetrahydrothiophenes
published pages: 14293-14296, ISSN: 1433-7851, DOI: 10.1002/anie.201708346
Angewandte Chemie International Edition 56/45 2019-06-06
2017 Alexander Lücht, Lukas J. Patalag, André U. Augustin, Peter G. Jones, Daniel B. Werz
Reactions of Donor-Acceptor Cyclopropanes with Naphthoquinones: Redox and Lewis Acid Catalysis Working in Concert
published pages: 10587-10591, ISSN: 1433-7851, DOI: 10.1002/anie.201703732
Angewandte Chemie International Edition 56/35 2019-06-06
2016 Jan Wallbaum, Lennart K. B. Garve, Peter G. Jones, Daniel B. Werz
Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes
published pages: , ISSN: 1521-3765, DOI: 10.1002/chem.201605265
Chemistry - A European Journal 2019-06-06
2017 Jan Wallbaum, Lennart K. B. Garve, Peter G. Jones, Daniel B. Werz
Ring-Opening 1,3-Halochalcogenation of Cyclopropane Dicarboxylates
published pages: , ISSN: 1523-7060, DOI: 10.1021/acs.orglett.6b03375
Organic Letters 2019-06-06

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