![1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure](https://static.chemtradehub.com/structs/122/1226872-27-0-e037.webp "1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone structure")
1-{3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl}-2,3-dihydroxy-1-propanone
CAS Number:
1226872-27-0
Molecular Formula:
C25H26N6O4
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
Literature Information
Publication Date
2023-10-17
DOI
10.1039/D3QO01263H
Impact Factor
5.281
Authors
Ting Wang, Zhi-Huan Peng, Liexin Wu, Qingwei Song, Qianying Li, Hui Gao, Zhongyi Zeng, Zhi Zhou, Wei Yi
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
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2-Methyl-2-propanyl 2-carbamimidoyl-1-piperidinecarboxylate
CAS Number:
1258640-98-0
Molecular Formula:
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