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Keywords = benzosultams

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4 pages, 903 KiB  
Short Note
2-((3R,9bS)-5,5-Dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one
by Yeongju Kim and Sung-Gon Kim
Molbank 2024, 2024(4), M1931; https://doi.org/10.3390/M1931 - 5 Dec 2024
Viewed by 881
Abstract
A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-cycloaddition of benzo[d]isothiazole 1,1-dioxide with (E)-4-hydroxy-1-phenylbut-2-en-1-one, using a bifunctional squaramide-based chiral [...] Read more.
A highly efficient method has been developed for preparing 2-((3R,9bS)-5,5-dioxido-2,3-dihydro-9bH-benzo[4,5]isothiazolo[3,2-b]oxazol-3-yl)-1-phenylethan-1-one. This enantioenriched title compound was obtained via an organocatalytic asymmetric [3+2]-cycloaddition of benzo[d]isothiazole 1,1-dioxide with (E)-4-hydroxy-1-phenylbut-2-en-1-one, using a bifunctional squaramide-based chiral catalyst. The reaction yielded 99% of the product with high enantioselectivity and diastereoselectivity (89:11 er and >20:1 dr). The structure of the newly synthesized compound was confirmed by 1H-, 13C-NMR, IR and mass spectral data. Full article
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21 pages, 7840 KiB  
Review
Recent Advances in Catalytic Synthesis of Benzosultams
by Quan-Qing Zhao and Xiao-Qiang Hu
Molecules 2020, 25(19), 4367; https://doi.org/10.3390/molecules25194367 - 23 Sep 2020
Cited by 36 | Viewed by 4120
Abstract
Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems [...] Read more.
Benzosultams represent one category of multi-heteroatom heterocyclic scaffolds, which have been frequently found in pharmaceuticals, agricultural agents, and chiral catalysts. Given the diversely significant functions of these compounds in organic and medicinal chemistry, great efforts have been made to develop novel catalytic systems for the efficient construction of benzosultam motifs over the past decades. Herein, in this review, we mainly summarize the recent advances in the field of catalytic synthesis of benzosultams from 2017 to August of 2020, with an emphasis on the scopes and mechanisms of representative reactions. Full article
(This article belongs to the Special Issue Non-Natural Multi-Heteroatom Heterocycles: New Chemical Space)
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