Access to phosphorus-containing cyclopenta[b]benzofuranols via a serendipitous cascade reaction promoted by a bifunctional phosphonium salt
Literature Information
Publication Date
2023-08-07
DOI
10.1039/D3QO00979C
Impact Factor
5.281
Authors
Hui-Lin Hu, Siqiang Fang, Yulin Chen, Wei Wan, Yuqiao Zhou, Zhipeng Xu, Tianli Wang
View Original
Abstract
In the current work, we serendipitously discovered a cascade reaction of readily available flavonoid derivatives with phosphine oxides by harnessing a bifunctional phosphonium salt catalyst, affording a variety of architecturally complex cyclopenta[b]benzofuranols with phosphorus-containing units in good yields. Mechanistic investigations revealed that this cascade process involved a cumulative diene as the key intermediate. Furthermore, an initial study of an asymmetric version of this reaction was conducted, in which the chiral product was generated in moderate yield with moderate enantioselectivity.
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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
Recommended Compounds
N-Methyl-3-(1-naphthyloxy)-3-(2-thienyl)-1-propanamine hydrochloride (1:1)
CAS Number:
1188266-11-6
Molecular Formula:
C18H20ClNOS
![N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure](https://static.chemtradehub.com/structs/210/2101206-92-0-2eb5.webp "N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide structure")
N-{15-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-15-oxo-3,6,9,12-tetraoxapentadec-1-yl}-2-(2-propyn-1-yloxy)acetamide
CAS Number:
2101206-92-0
Molecular Formula:
C20H30N2O10
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