Issue 18, 2017
From the journal:

Chemical Communications

Brønsted acid-catalyzed stereoselective [4+3] cycloadditions of ortho-hydroxybenzyl alcohols with N,N′-cyclic azomethine imines†

Guang-Jian Mei,‡a   Zi-Qi Zhu,‡a   Jia-Jia Zhao,a   Chen-Yu Bian,a   Jie Chen,a   Ruo-Wei Chena  and  Feng Shi ORCID logo *a  

* Corresponding authors

a School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, China
E-mail: fshi@jsnu.edu.cn
Tel: +86(516) 83403183

Abstract

The first [4+3] cycloaddition of ortho-hydroxybenzyl alcohols has been established by making use of N,N′-cyclic azomethine imines as suitable 1,3-dipoles under Brønsted acid catalysis. By using this strategy, biologically important seven-membered heterocyclic scaffolds have been constructed in good yields and excellent diastereoselectivities (up to 92% yield, most >95 : 5 dr).

Graphical abstract: Brønsted acid-catalyzed stereoselective [4+3] cycloadditions of ortho-hydroxybenzyl alcohols with N,N′-cyclic azomethine imines

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Article information

DOI
https://doi.org/10.1039/C6CC09775H
Article type
Communication
Submitted
08 Dec 2016
Accepted
06 Feb 2017
First published
08 Feb 2017

Chem. Commun., 2017,53, 2768-2771

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Brønsted acid-catalyzed stereoselective [4+3] cycloadditions of ortho-hydroxybenzyl alcohols with N,N′-cyclic azomethine imines

G. Mei, Z. Zhu, J. Zhao, C. Bian, J. Chen, R. Chen and F. Shi, Chem. Commun., 2017, 53, 2768 DOI: 10.1039/C6CC09775H

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