Issue 58, 2016, Issue in Progress
From the journal:

RSC Advances

Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7†

Jiadong Hu,a   Dongyang Xu,b   Qiang Zhang,c   Yang Shang,b   Mumin Shi,c   Yucui Huangfu,c   Leilei Liu,c   Rong liang,c   Yisheng Lai,*a   Yupeng He,*b   Jin-ming Gaoc  and  Weiqing Xie*cd  

* Corresponding authors

a State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Center of Drug Discovery, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China
E-mail: yslai@cpu.edu.cn
Fax: +86-025-83271015
Tel: +86-025-83271015

b College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, China
E-mail: yupeng.he@lnpu.edu.cn

c Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University, 22 Xiong Road, Yangling 712100, Shanxi, China
E-mail: xiewq@sioc.ac.cn

d State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

Abstract

Re2O7 catalyzed tandem allylic alcohol isomerization/oxa-Michael addition reaction of cyclohexadienone was developed. The reaction features a regioselective and stereoselective isomerization of allylic alcohol and diastereoselective ring closure via oxa-Michael addition. This method also enabled construction of enantiopure bicyclic enones from substrates incorporated with chiral allylic alcohol via efficient chirality transfer.

Graphical abstract: Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7

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Article information

DOI
https://doi.org/10.1039/C6RA10399E
Article type
Communication
Submitted
22 Apr 2016
Accepted
23 May 2016
First published
25 May 2016

RSC Adv., 2016,6, 52583-52586

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Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7

J. Hu, D. Xu, Q. Zhang, Y. Shang, M. Shi, Y. Huangfu, L. Liu, Rong liang, Y. Lai, Y. He, J. Gao and W. Xie, RSC Adv., 2016, 6, 52583 DOI: 10.1039/C6RA10399E

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