Synthesis of Selectively gem-Difluorinated Molecules; Chiral gem-Difluorocyclopropanes via Chemo-Enzymatic Reaction and gem-Difluorinated Compounds via Radical Reaction.

Radical reaction Ring closing metathesis Ring-opening Visible light gem-Difluorocyclopropane; gem-Difluoromethylene

Journal

Chemical record (New York, N.Y.)

ISSN: 1528-0691

Titre abrégé: Chem Rec

Pays: United States

ID NLM: 101085550

Informations de publication

Date de publication:
Sep 2023

Historique:

revised: 07 03 2023

received: 27 01 2023

medline: 23 3 2023

pubmed: 23 3 2023

entrez: 22 3 2023

Statut: ppublish

Résumé

The incorporation of fluorine atoms into an organic compound can alter the chemical reactivity or biological activity of the resulting compound due to the strong electron withdrawing nature of the fluorine atom. We have synthesized many original gem-difluorinated compounds and described the results in four sections. The first section describes the synthesis of optically active-gem-difluorocyclopropanes via the chemo-enzymatic reaction; we applied these compounds to liquid crystalline molecules, then further discovered a potent DNA cleavage activity for the gem-difluorocyclopropane derivatives. The second section describes the synthesis of selectively gem-difluorinated compounds via a radical reaction; we synthesized fluorinated analogues of a sex pheromone of the male African sugarcane borer, Eldana saccharina, and used the compounds as proof for investigating the origin of pheromone molecule recognition on the receptor protein. The third involves the synthesis of 2,2-difluorinated-esters by visible light-driven radical addition of 2,2-difluoroacetate with alkenes or alkynes in the presence of an organic pigment. The last section describes the synthesis of gem-difluorinated compounds via the ring-opening of gem-difluorocyclopropanes. We further developed a novel method of synthesizing gem-difluorohomoallylic alcohols via the ring-opening of gem-difluorocyclopropane and aerobic oxidation by photo-irradiation in the presence of an organic pigment. Since gem-difluorinated compounds that were prepared by the present method have two olefinic moieties with a different reactivity at the terminal position, we accomplished the synthesis of four types of gem-difluorinated cyclic alkenols via the ring-closing-metathesis (RCM) reaction.

Identifiants

DOI: 10.1002/tcr.202300028 PMID: 36949016

pubmed: 36949016

doi: 10.1002/tcr.202300028

doi:

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

Pagination

e202300028

Subventions

Organisme : JSPS Kakenhi

Informations de copyright

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