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RACING SIGNED

Rapid access to functionalized cyclobutanes via ring expansion strategies

Total Cost €

0

EC-Contrib. €

0

Partnership

0

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 RACING project word cloud

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

ligands    host    normally    alpha    chemistry    vinyl    chiral    forging    combination    proposing    esters    bioactive    larger    solid    contributed    radicals    motifs    academic    boronate    containing    enantioenriched    compounds    electrophile    plan    smaller    pi    rings    leaving    networks    significantly    alkenyl    orient    researcher    boronic    construct    functionalized    rearrangements    photoredox    acidic    lay    synthesis    catalysis    valuable    reactions    halogens    cyclobutanes    metallate    strategy    precise    vectors    boron    boronates    transfer    fundamentally    shifts    mechanistic    transition    natural    photoreaction    cyclopropyl    last    activated    expansion    group    scope    chemical    cyclobutyl    considerable    consequently    transformed    decade    substituents    organic    foundations    metals    medicinal    desirable    community    physical    found    scientific    groups    ring    discovery    rearrangement    palladium    benefit    migration    metal    carefully    versatile    herein    functional    induce    ester    complexes   

Project "RACING" 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]
 Total cost 224˙933 €
 EC max contribution 224˙933 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2018
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2019
 Duration (year-month-day) from 2019-04-01   to  2021-03-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 224˙933.00

Map

 Project objective

Cyclobutanes are common motifs in natural products and are increasingly important in medicinal chemistry since they can orient substituents along precise vectors. However, methods to construct cyclobutanes are less developed in comparison to their smaller and larger rings. Consequently, novel methods to access functionalized cyclobutanes are highly desirable and would be of considerable value for the discovery of new bioactive compounds. In the last decade, the host group and others have contributed significantly to the development of boron 1,2-migration chemistry which has found numerous applications in organic synthesis. Normally, 1,2-metallate shifts in boronate complexes are induced by α-leaving groups or by reactions of alkenyl boronates with halogens, π-acidic metals, or radicals. Herein, we are proposing a fundamentally new strategy to induce 1,2-metallate rearrangement, via a ring expansion of vinyl cyclopropyl boronate complex activated by an electrophile or by photoredox or transition metal catalysis. This novel process would lead to highly versatile boronic ester containing cyclobutanes, which can be transformed into other valuable functional groups. Furthermore, we plan to use chiral ligands in combination with palladium catalysis in this novel process, leading to enantioenriched chiral cyclobutyl boronic esters. These novel methodologies not only benefit from the formation of highly functionalized cyclobutanes, but also lay solid foundations for the development of other ring-expansion induced 1,2-metallate rearrangements. The scope of these processes will be carefully investigated, and mechanistic studies of the photoreaction will be carried out using advanced physical/chemical methods. Finally, this project will enable significant knowledge transfer between the host and researcher, while forging new academic networks within the scientific community.

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