Synthesis of 2-cyclopropyl-4-pyrones and 5-cyclopropyl-2-alkylene-3(2H)-furanones based on tandem cyclization-cyclopropanation strategy

In AgSbF6/Rh2(OAc)4/DCE system, two-component diastereoselective reactions of 2-diazo-3,5-dioxo-6-ynoates (phosphonates and sulphones) and alkenes provided easy access to 2-cyclopropyl-γ-pyrones through 6-endo-dig cyclization-cyclopropanation. In AgOAc/Rh2(OAc)4/Et3N/DCE system, two-component reacti...

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Bibliographic Details
Published in:Tetrahedron 2019-02, Vol.75 (7), p.855-861
Main Authors: Liu, Weishun, Fang, Lin, Wan, Yinbo, Zhang, Jianfang, Deng, Guisheng, Wang, Jianbo
Format: Article
Language:English
Subjects:
4-Pyranone
Acid
Alkylene-3(2H)-furanones
Catalysis
Cyclization
Cyclopropanation
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Summary:In AgSbF6/Rh2(OAc)4/DCE system, two-component diastereoselective reactions of 2-diazo-3,5-dioxo-6-ynoates (phosphonates and sulphones) and alkenes provided easy access to 2-cyclopropyl-γ-pyrones through 6-endo-dig cyclization-cyclopropanation. In AgOAc/Rh2(OAc)4/Et3N/DCE system, two-component reaction of 2-diazo-3,5-dioxo-7-aryl-6-ynoates and alkenes afforded 2-cyclopropyl-2-alkylene-3(2H)-furanones through 5-exo-dig cyclization-cyclopropanation. The possible mechanism of reaction is discussed. A simple procedure and mild conditions are significant features of this strategy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.11.063