Issue 55, 2018
From the journal:

Chemical Communications

A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement†

Ming-Hui Xu,a   Kun-Long Dai,a   Yong-Qiang Tu, ORCID logo *ab   Xiao-Ming Zhang, ORCID logo *a   Fu-Min Zhanga  and  Shao-Hua Wang ORCID logo a  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry & School of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China
E-mail: tuyq@lzu.edu.cn

b School of Chemistry & Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China
E-mail: tuyq@sjtu.edu.cn

Abstract

A catalytic intermolecular semipinacol rearrangement induced by allylic carbocations has been realized. This tandem reaction is highly efficient under the catalysis of ZnBr2, generating a wide range of α-homoallyl substituted ketones which contain all-carbon quaternary centres in good to excellent yields (up to 98%) with moderate to high diastereoselectivities (up to >20 : 1). Synthetic application of this novel methodology in the construction of core structures of natural products is also reported.

Graphical abstract: A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement

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Article information

DOI
https://doi.org/10.1039/C8CC04285C
Article type
Communication
Submitted
29 May 2018
Accepted
18 Jun 2018
First published
19 Jun 2018

Chem. Commun., 2018,54, 7685-7688

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A catalytic allylic cation-induced intermolecular allylation-semipinacol rearrangement

M. Xu, K. Dai, Y. Tu, X. Zhang, F. Zhang and S. Wang, Chem. Commun., 2018, 54, 7685 DOI: 10.1039/C8CC04285C

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