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FOOTLOOSE SIGNED

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

Total Cost €

0

EC-Contrib. €

0

Partnership

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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.

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

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

 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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