Copper-Catalyzed Phosphonation–Annulation Approaches to the Synthesis of β‑Phosphonotetrahydrofurans Involving C–P and C–O Bonds Formation

Substituted tetrahydrofuran derivatives play important roles as biological activities. A versatile method for the synthesis of β-phosphonotetrahydrofurans has been developed based on Cu-catalyzed difunctionalization of alkenes. This transformation would provide a new pathway for the formation of Csp...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-11, Vol.80 (22), p.11398-11406
Main Authors: Gao, Yuzhen, Li, Xueqin, Chen, Weizhu, Tang, Guo, Zhao, Yufen
Format: Article
Language:English
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Summary:Substituted tetrahydrofuran derivatives play important roles as biological activities. A versatile method for the synthesis of β-phosphonotetrahydrofurans has been developed based on Cu-catalyzed difunctionalization of alkenes. This transformation would provide a new pathway for the formation of Csp3–P and Csp3–O bonds in one step. Furthermore, this copper catalyst system can be used in the synthesis of β-phosphonotetrahydropyrans and phosphono-γ-butyrolactones. These reactions were also performed well by using 3 equiv of Mn­(OAc)3·2H2O as the oxidant without copper catalyst.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02026