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

Yuzhen Gao; Xueqin Li; Weizhu Chen; Guo Tang; Yufen Zhao

doi:10.1021/acs.joc.5b02026

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

J Org Chem. 2015 Nov 20;80(22):11398-406. doi: 10.1021/acs.joc.5b02026. Epub 2015 Nov 11.

Authors

Yuzhen Gao¹, Xueqin Li¹, Weizhu Chen^{1

2}, Guo Tang¹, Yufen Zhao¹

Affiliations

¹ Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University , Xiamen, Fujian 361005, China.
² Third Institute of Oceanography, State Oceanic Administration , Xiamen, Fujian 361005, China.

PMID: 26523923
DOI: 10.1021/acs.joc.5b02026

Abstract

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(3)-P and Csp(3)-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.

Publication types

Research Support, Non-U.S. Gov't