![1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure](https://cnstatic.chemtradehub.com/structs/603/60373-71-9-7dfb.webp "1-(1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-benzo[d]imidazol-2(3H)-one structure")
N-Heterocyclic carbene catalyzed base assisted C–C bond cleavage of cyclopropenones: an approach towards diastereoselective synthesis of azetidinones and benzoxazepines
文献信息
发布日期
2023-10-25
DOI
10.1039/D3QO01328F
影响因子
5.281
作者
查看原文
摘要
N-Heterocyclic carbene catalyzed base assisted diastereoselective ring opening of diphenyl-cyclopropenone followed by ring-closing through [3 + 1] or [3 + 4] addition with o-aminophenol furnished biologically important scaffolds azetidinones or benzoxazepines, respectively. The unique feature of this reaction is that the key intermediate acylazolium species is generated through C–C bond cleavage of cyclopropenone rather than routine substrates such as conjugated enals, ynals and acyl halides. Interestingly, this reaction involves an α-aryl substituted acylazolium species, which has never been reported so far with respect to N-heterocyclic carbene catalysis.
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来源期刊
Organic Chemistry Frontiers
CiteScore:
7.8
自引率:
8.7%
年发文量:
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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