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A Versatile Organocatalytic Approach for the Synthesis of Enantioenrichedgem-Difluorinated Compounds

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Saulnier, Steve Ciardi, Moira [UCL] Lopez-Carrillo, Veronica Gualandi, Andrea Cozzi, Pier Giorgio

The combination of a practical and highly enantioselective organocatalytic reaction, which allows the stereoselective introduction of a benzodithiol group, with a fluorination step, gives a new and effective strategy for the stereoselective synthesis of difluorinated building blocks. The benzodithiol group is a versatile and chameleonic group that can be further functionalized before fluorination, giving customized and tailored useful synthetic strategies. As an example of the application of this facile strategy, the effective enantioselective synthesis of difluoroarundic acid is described. All you need is fluor! The combination of a practical and highly enantioselective organocatalytic reaction with a fluorination step provides a new and effective strategy for the stereoselective synthesis of enantioenriched difluorinated building blocks (see scheme).

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2015
Language Anglais
Journal information "Chemistry: A European Journal" - Vol. 21, no.39, p. 13689-13695 (2015)
Peer reviewed yes
Publisher Wiley-VCH Verlag ((Germany) Weinheim)
issn 0947-6539
e-issn 1521-3765
Publication status Publié
Affiliation UCL - SST/IMCN/BSMA - Bio and soft matter
Keywords Aldehydes ; Alkylation ; Enantioselectivity ; Fluorine ; Organocatalysis
Links
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Bibliographic reference Saulnier, Steve ; Ciardi, Moira ; Lopez-Carrillo, Veronica ; Gualandi, Andrea ; Cozzi, Pier Giorgio. A Versatile Organocatalytic Approach for the Synthesis of Enantioenrichedgem-Difluorinated Compounds. In: Chemistry: A European Journal, Vol. 21, no.39, p. 13689-13695 (2015)
Permanent URL http://hdl.handle.net/2078.1/173182