Enantio-, Diastereo- and Regioselective Synthesis of Chiral Cyclic and Acyclic gem-Difluoromethylenes by Palladium-Catalyzed [4+2] Cycloaddition.
Asymmetric Catalysis
Cycloaddition
Enantioselectivity
Palladium
gem-Difluoroalkyl
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
13 06 2022
13 06 2022
Historique:
received:
27
12
2021
pubmed:
29
3
2022
medline:
31
5
2022
entrez:
28
3
2022
Statut:
ppublish
Résumé
gem-Difluoromethylene moieties are attractive in medicinal chemistry due to their ability to mimic other more ubiquitous functional groups. Thus, effective asymmetric methods for their construction are highly desirable, especially for the industrial production of chiral drugs. Using a Pd-catalyzed asymmetric [4+2] cycloaddition between substituted-2-alkylidenetrimethylene carbonates and gem-difluoroalkyl ketones, we were able to easily access chiral 1,3-dioxanes that contain a tetrasubstituted difluoroalkyl stereogenic center in cyclic and acyclic skeletons. A novel phosphoramidite ligand, which contains a bulky 1,1-dinaphthylmethanamino moiety, was developed to provide the products in high yield with excellent enantio-, diastereo-, and regioselectivity. Strikingly, the gem-difluoro substitution pattern promotes the reaction, and pentafluoroethylketone, an α,α-difluorinated β-ketoester, and a β-ketosulfone are suitable substrates for this method.
Identifiants
pubmed: 35344247
doi: 10.1002/anie.202117635
doi:
Substances chimiques
Hydrocarbons, Fluorinated
0
Palladium
5TWQ1V240M
difluoromethane
77JW9K722X
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202117635Informations de copyright
© 2022 Wiley-VCH GmbH.
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Deposition Number 2123342 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Deposition Number 2123343 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
Deposition Number 2130769 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
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Deposition Number 2123344 contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.