Nickel‐Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl‐Substituted 1,6‐Enynes for the Synthesis of Seletracetam

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(46)

Опубликована: Сен. 23, 2022

Abstract The introduction of fluorine‐containing groups into organic molecules can significantly affect their physical and chemical properties has long been used as an effective strategy for drug discovery development. Consequently, the development catalytic asymmetric methods synthesis heterocycles is highly desirable sought after. Herein, we describe a nickel‐catalyzed defluorinative cyclization fluoroalkyl‐substituted 1,6‐enynes, providing expedient access to synthetically attractive 4‐fluorovinyl‐substituted 2‐pyrrolidones in good yields with remarkable high levels chemo‐, regio‐, enantioselectivities (90–99 % ee,>35 examples). This protocol features readily available starting materials excellent functional group compatibility, exhibits complementary regioselectivity. utility this was demonstrated enantioselective antiepileptic Seletracetam.

Язык: Английский

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Progress in Trifluoromethylation Reaction of Olefins

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134545 - 134545

Опубликована: Март 1, 2025

Язык: Английский

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Selective single C–F bond arylation of trifluoromethylalkene derivatives

Chemical Science, Год журнала: 2019, Номер 10(37), С. 8701 - 8705

Опубликована: Янв. 1, 2019

A strategically novel single C-F bond functionalization of CF3-derived molecules, which shows a prominent advantage for the expedient construction difluoromethylene-bridged organic scaffolds, is disclosed. The reported protocol consists SN2' amination, N-alkylation and palladium-catalyzed allylic substitution reactions, enables straightforward arylation alkenylation vinyltrifluoromethane derivatives. Furthermore, this strategy characterized by its broad substrate scope with respect to both CF3-alkene arylboronic acid

Язык: Английский

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Rhodium‐Catalyzed Enantioselective Defluorinative α‐Arylation of Secondary Amides

Angewandte Chemie International Edition, Год журнала: 2018, Номер 57(49), С. 16147 - 16151

Опубликована: Окт. 10, 2018

Abstract We exploited the reactivity of an electronically biased Michael acceptor to perform a defluorinative α‐arylation reaction using chiral diene(L*)‐rhodium catalyst. Through this methodology, we are able obtain various secondary amides, containing tertiary α‐stereocenter and β,γ‐unsaturated gem ‐difluoro olefin, with excellent enantioselectivities. This methodology addresses limitations previously described methods construct stereo‐labile α‐stereocenters. Further investigation via in situ 19 F NMR monitoring suggests that formation product leads inhibition active rhodium

Язык: Английский

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Cu-Catalyzed Regio- and Stereodivergent Chemoselective sp/sp 1,3- and 1,4-Diborylations of CF3-Containing 1,3-Enynes

Chem, Год журнала: 2020, Номер 6(9), С. 2347 - 2363

Опубликована: Июль 23, 2020

Язык: Английский

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