Synthesis 2012; 44(13): 2049-2057
DOI: 10.1055/s-0031-1291152
paper
© Georg Thieme Verlag Stuttgart · New York

Gold-Catalyzed Skeletal Rearrangement of 1-[2-(1H-Isochromen-3-yl)aryl]ethanones with Alcohols

Wen-Ting Wei
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
b   Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
,
Peng Xie
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
b   Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
,
Jia-Dong Xia
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
b   Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
,
Ye-Xiang Xie*
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
,
Ren-Jie Song
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
,
Jian-Nan Xiang
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
,
Jin-Heng Li*
a   College of Chemistry and Chemical Engineering, and State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, P. R. of China , Fax: +86(731)88872101   Email: jhli@hnu.edu.cn   Email: xieyexiang520@126.com
› Author Affiliations
Further Information

Publication History

Received: 07 March 2012

Accepted after revision: 19 April 2012

Publication Date:
01 June 2012 (online)


Abstract

A novel gold-catalyzed skeletal rearrangement of 1-[2-(1H-isochromen-3-yl)aryl]ethanones with alcohols to construct a five-membered carbocycle ring onto aromatic systems has been developed. This method serves as the first example of synthesizing inden-1-ones by a gold-catalyzed skeletal rearrangement strategy.

Supporting Information

 
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  • 10 The X-ray single-crystal diffraction analysis of 16 is given in the Supporting Information