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FOOTLOOSE SIGNED

Synthesis of sp3-Rich Organofluorine Compounds through Homologation of Boronic Esters

Total Cost €

0

EC-Contrib. €

0

Partnership

0

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 FOOTLOOSE project word cloud

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

protocol    benzoates    preparation    lithiation    owing    group    medicinal    stone    closer    stage    atom    sparteine    laboratory    chemical    manner    lithiated    secondary    formed    primary    chains    exquisite    carbamates    modifications    stability    conformational    landscape    sought    exchange    line    boronic    attractive    bond    sharpening    enantioselective    size    absolute    configuration    oh    outline    molecule    synthesis    borylation    programs    diverse    stereoselective    works    ideal    imparted    groups    compounds    enantiospecific    mediated    assembly    temperature    host    lithium    electronegative    atoms    organofluorine    carbon    trifluoromethyl    homologation    oxygen    hit    either    pure    relative    esters    substituted    shown    deprotonation    latter    molecules    tin    chain    chemistry    grown    bonds    stereochemically    rewarding    advantage    enriched    bearing    replacement    small    made    herein    substituents    fluorine    enantiomerically    incorporation    dependent    time    big    containing    iterative    introduce   

Project "FOOTLOOSE" 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 http://www.chm.bris.ac.uk/org/aggarwal/research.php
 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-2016
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2017
 Duration (year-month-day) from 2017-07-27   to  2019-07-26

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITY OF BRISTOL UK (BRISTOL) coordinator 183˙454.00

Map

Leaflet | Map data © OpenStreetMap contributors, CC-BY-SA, Imagery © Mapbox

 Project objective

Organofluorine compounds are highly sought after owing to diverse and numerous applications that take advantage of the unique properties imparted by the presence of one or more C–F bonds. The chemical stability and conformational landscape of molecules, together with the small size of the fluorine atom, has the made the replacement of a C–H or C–OH bond with a C–F one of the most rewarding modifications during the hit-to-lead stage in medicinal chemistry programs. Because many applications are dependent on the absolute and relative configuration of the fluorine-containing group, methods that can introduce such groups in a stereoselective manner are particularly attractive. The host laboratory has shown that substituted carbon chains can be grown one carbon atom at a time with exquisite control of relative and absolute configuration through iterative homologation of boronic esters with stereochemically-defined lithiated carbamates or benzoates. The latter are formed at low temperature, either through sparteine-mediated enantioselective deprotonation of primary carbamates/benzoates or the enantiospecific deprotonation or tin–lithium exchange of enantiomerically pure secondary carbamates/ benzoates. Although the process works well for extending a carbon chain with incorporation of carbon-based substituents, the incorporation of carbon atoms bearing electronegative substituents, such as oxygen- or fluorine-containing groups, is challenging. Herein we propose a programme of research to investigate the preparation of enantiomerically enriched organofluorine molecules, specifically those containing trifluoromethyl groups, through lithiation–borylation. The challenges outline above would make such a programme the ideal sharpening stone for the further development of lithiation–borylation. Indeed, a protocol that can introduce carbon atoms bearing electronegative groups would bring us a big step closer to assembly-line synthesis being able to make any molecule.

 Publications

year authors and title journal last update
List of publications.
2018 Roly J. Armstrong, Meganathan Nandakumar, Rafael M. P. Dias, Adam Noble, Eddie L. Myers, Varinder K. Aggarwal
Enantiodivergent Synthesis of Allenes by Point-to-Axial Chirality Transfer
published pages: 8203-8208, ISSN: 1433-7851, DOI: 10.1002/anie.201804446
Angewandte Chemie International Edition 57/27 2020-04-14

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