Elsevier

Tetrahedron Letters

Volume 54, Issue 25, 19 June 2013, Pages 3294-3297
Tetrahedron Letters

A singlet oxygen approach to oxaspirocycles

https://doi.org/10.1016/j.tetlet.2013.04.064Get rights and content

Abstract

A method for the preparation of oxygen containing spirocycles using singlet oxygen is reported. A series of phenols were converted into the corresponding peroxy-cyclohexadienone derivatives by irradiation with visible light in the presence of a sensitizer and oxygen. The resulting peroxides could be converted into ether and lactone spirocycles in one or two steps. The synthesis of the oxaspirocycles from the phenols can also be performed in a one-pot fashion, avoiding the isolation of the peroxide intermediates.

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Acknowledgments

The authors gratefully acknowledge the financial support from the DFG (Heisenberg scholarship to M.K., KL 2221/4-1), the Alexander von Humboldt Foundation (scholarship to K.M.J) and Prof. Benjamin List, as well as help in performing the one-pot reaction from Esther Boess.

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