PtI2-Catalyzed tandem 3,3-rearrangement/Nazarov reaction of arylpropargylic esters: synthesis of indanone derivatives

Huaiji Zheng; Xingang Xie; Juan Yang; Changgui Zhao; Peng Jing; Bowen Fang; Xuegong She

doi:10.1039/C1OB06138K

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PtI₂-Catalyzed tandem 3,3-rearrangement/Nazarov reaction of arylpropargylic esters: synthesis of indanone derivatives†

Huaiji Zheng,^a Xingang Xie,^a Juan Yang,^a Changgui Zhao,^a Peng Jing,^a Bowen Fang^a and Xuegong She*^ab

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Gansu, P. R. China

^b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physic, Chinese Academy of Sciences Lanzhou, Gansu, P. R. China
E-mail: shexg@lzu.edu.cn
Fax: (+86)931-8912582

Abstract

An efficient PtI₂-catalyzed tandem reaction of arylpropargylic esters, involving 3,3-rearrangement and Nazarov reaction, has been developed to produce 3-substituted and 3,3-disubstituted indanone derivatives. This approach provided a pathway to the synthesis of indanone skeletons in natural products.

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Article information

DOI: https://doi.org/10.1039/C1OB06138K
Article type: Paper
Submitted: 11 Jul 2011
Accepted: 18 Aug 2011
First published: 18 Aug 2011

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Org. Biomol. Chem., 2011,9, 7755-7762

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PtI₂-Catalyzed tandem 3,3-rearrangement/Nazarov reaction of arylpropargylic esters: synthesis of indanone derivatives

H. Zheng, X. Xie, J. Yang, C. Zhao, P. Jing, B. Fang and X. She, Org. Biomol. Chem., 2011, 9, 7755 DOI: 10.1039/C1OB06138K

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Organic & Biomolecular Chemistry