Rh(iii)-catalyzed redox-neutral C–H [4 + 1] annulation of sulfoximines with α,α-difluoromethylene alkynes: diastereoselective synthesis of E-monofluoroalkenyl benzoisothiazole 1-oxides

文献情報

出版日 2023-10-17

DOI 10.1039/D3QO01263H

インパクトファクター 5.281

著者

Ting Wang, Zhi-Huan Peng, Liexin Wu, Qingwei Song, Qianying Li, Hui Gao, Zhongyi Zeng, Zhi Zhou, Wei Yi

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要旨

Novel cyclic fluorinated sulfoximines featuring an E-monofluoroalkenyl benzoisothiazole 1-oxide moiety as single diastereomers can be facilely accessed by Rh(III)-catalyzed redox-neutral [4 + 1] annulation of sulfoximines with α,α-difluoromethylene alkynes. The reaction proceeds with sequential selective cleavage of both C–H and C–F bonds, thus exhibiting high step and atom economy. Through a combined experimental and computational mechanistic study, the origins of annulative chemoselectivity, unconventional E-selectivity, and excellent diastereoselectivity have been revealed accordingly.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Rh(iii)-catalyzed redox-neutral C–H [4 + 1] annulation of sulfoximines with α,α-difluoromethylene alkynes: diastereoselective synthesis of E-monofluoroalkenyl benzoisothiazole 1-oxides

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The facile alkylation and iodination of imidazol(in)ium salts in the presence of cesium carbonate

Contributors to the Emerging Investigators collection 2023: Part 2

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