Synlett 2016; 27(20): 2774-2782
DOI: 10.1055/s-0036-1588085
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© Georg Thieme Verlag Stuttgart · New York

Research on the Conversion of α-Hydroxy Ketones into 1,2-Diketones and Subsequent Transformations

Hanbing Liang
a   School of Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. of China
,
Hui Liu*
a   School of Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, P. R. of China
,
Xuefeng Jiang*
b   Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, Shanghai 200062, P. R. of China   eMail: xfjiang@chem.ecnu.edu.cn
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Publikationsverlauf

Received: 07. August 2016

Accepted after revision: 05. Oktober 2016

Publikationsdatum:
27. Oktober 2016 (online)


Abstract

1,2-Diketone derivatives are valuable molecules which are widely applied in organic synthesis. In this account, we discuss our recent research progress on the construction of 1,2-diketone derivatives and their subsequent transformations, including the synthesis of ynediones, the dicarbonylation of indoles and the preparation of heterocyclic hemiketals from ynediones. In addition, mechanistic investigations on the dicarbonylation of α-hydroxy ketones are described and plausible mechanisms are proposed. Furthermore, the synthesis of 3(2H)-furanones and 3(2H)-thienones from ynediones are also described.

1 Introduction

2 A Copper-Catalyzed One-Pot Approach Toward Ynediones

3 Copper-Catalyzed Aerobic Oxidative Dicarbonylation of Indoles

4 Synthesis of Heterocyclic Hemiketals from Ynediones

5 Conclusion

 
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