Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Март 3, 2025

A highly enantioselective electrophilic selenylation/semipinacol rearrangement of allenols has been developed, which is enabled by the cooperative catalysis a chiral sulfide and an achiral sulfonic acid. The designed synthesized catalyst selenylating reagent play crucial role in enhancing both enantioselectivity reactivity. This approach exhibits excellent regio-, chemo-, enantioselectivity, providing access to diverse enantioenriched cyclopentanones featuring arylselenovinyl-substituted quaternary carbon stereocenter. Furthermore, these products can be transformed into synthetically valuable alkyne, vinyl bromide, aniline derivatives. Mechanistic studies reveal that combination acid not only facilitates formation catalytically active species, but also governs reaction. Meanwhile, density functional theory calculations disclose four hydrogen bond interactions π‧‧‧π interaction are responsible for observed enantioselectivity. Rearrangement reactions serve as steps syntheses biologically provide intellectual conceptual curiosities within broad field organic chemistry. Here, authors report allenols, catalysed Lewis base.

Язык: Английский

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Organocatalytic Atroposelective Hydroselenation of Alkynes To Access Axially Chiral Vinyl Selenides

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 4051 - 4060

Опубликована: Фев. 20, 2025

Язык: Английский

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Allylic Acetal as 3C Synthon in Rh(III)-Catalyzed Divergent C–H Activation/[4 + 3] Annulation: Easy Access to Benzodiazepines

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 2, 2025

A concise synthesis of benzodiazepines via Rh(III) catalyzed C-H activation/ [4 + 3] annulation easily available 1-arylpyrazolidinones with allylic acetal has been developed. The was employed as a novel 3C synthon in this transformation. Benzodiazepines were built under mild reaction conditions high efficiency and chemoselectivity. atom-economy accessible substrates reveal potential application.

Язык: Английский

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Organocatalytic Asymmetric Electrophilic Tandem Selenylation Semipinacol Rearrangement of 1-(1-Arylvinyl)cyclobutanols

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Chiral BINAM-derived sulfide and boron trifluoride etherate cocatalyzed enantioselective electrophilic selenylation/semipinacol rearrangement of 1-(1-arylvinyl)cyclobutanols was developed for the first time.

Язык: Английский

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Catalyst-Controlled Divergent Cyclopropene Hydroselenation

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 8855 - 8864

Опубликована: Май 11, 2025

Язык: Английский

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