Issue 19, 2016
From the journal:

Organic & Biomolecular Chemistry

Silver-promoted cinnamamidyl radical-mediated oxidative cascade cyclization: highly regioselective synthesis of phosphorylated azaspiro[4.5]decenones†

Zhao-Zhao Zhou,a   Lan Zheng,a   Xiao-Biao Yan,a   Dong-Po Jin,a   Yu-Tao Hea  and  Yong-Min Liang*ab  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, P.R. China
E-mail: liangym@lzu.edu.cn
Fax: (+86) 931-891-2582

b State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Science, Lanzhou, P.R. China

Abstract

A silver-promoted oxidative cascade cyclization with a phosphorylation/1,5-aryl migration/desulfonylation/dearomatization process is presented here, providing an efficient method to synthesize azaspiro[4.5]decenones with high regioselectivity. The cinnamamidyl radical, which has rarely been reported before, plays a key role in this reaction.

Graphical abstract: Silver-promoted cinnamamidyl radical-mediated oxidative cascade cyclization: highly regioselective synthesis of phosphorylated azaspiro[4.5]decenones

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Article information

DOI
https://doi.org/10.1039/C6OB00505E
Article type
Paper
Submitted
05 Mar 2016
Accepted
13 Apr 2016
First published
13 Apr 2016

Org. Biomol. Chem., 2016,14, 4507-4510

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Silver-promoted cinnamamidyl radical-mediated oxidative cascade cyclization: highly regioselective synthesis of phosphorylated azaspiro[4.5]decenones

Z. Zhou, L. Zheng, X. Yan, D. Jin, Y. He and Y. Liang, Org. Biomol. Chem., 2016, 14, 4507 DOI: 10.1039/C6OB00505E

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