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Exploring molecular antipodes with flow chemistry
Monbaliu, Jean-Christophe
2017In Monbaliu, Jean-Christophe (Ed.) FROST 6
Peer reviewed
 

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Keywords :
Flow Chemistry; Reaction Telescoping; Chemical Ligation
Abstract :
[en] This lecture illustrates our work in flow chemistry with chemicals at the antipodes of molecular complexity. The first example deals with the valorization of biomass-derived small platform molecules, and in particular the implementation of a deoxydehydration (DODH) reaction of glycerol towards allyl alcohol under continuous-flow conditions. The combination of a unique reactive dynamic feed solution approach and short exposure to high temperature gave high yield and excellent selectivity in the presence of formic acid, triethyl orthoformate, or a combination of both. The second example deals with the preparation of large bio macromolecules, and in particular the implementation of chemical native ligation towards peptide constructs under continuous-flow conditions. The combination of the unique assets of microfluidic reactors and the development of new reagents/conditions were exploited to perform extremely fast ligations at difficult junctions that are notoriously time-consuming. Ligation times down to 2 min were achieved, with excellent conversion and overall isolated yields for a range of macrocylic peptides bearing up to 29 residues. The reaction conditions were also amenable, upon minor adjustments, to less hindered junctions.
Disciplines :
Chemistry
Author, co-author :
Monbaliu, Jean-Christophe  ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Language :
English
Title :
Exploring molecular antipodes with flow chemistry
Publication date :
2017
Event name :
Frontiers in Organic Synthesis Technology (FROST) 6
Event organizer :
Flow Chemistry Society
Event place :
Budapest, Hungary
Event date :
18-19-20/10/2017
By request :
Yes
Audience :
International
Main work title :
FROST 6
Author, co-author :
Monbaliu, Jean-Christophe  ;  Université de Liège - ULiège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis
Publisher :
Flow Chemistry Society
Peer reviewed :
Peer reviewed
Available on ORBi :
since 20 October 2017

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