Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines

Yingying Zhao; Chunxiang Wang; Yancheng Hu; Boshun Wan

doi:10.1039/C8CC00881G

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Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines†

Yingying Zhao,^ab Chunxiang Wang,

^a Yancheng Hu*^a and Boshun Wan

*^a

Author affiliations

* Corresponding authors

^a Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China
E-mail: ychu@dicp.ac.cn, bswan@dicp.ac.cn

^b University of Chinese Academy of Sciences, Beijing 10049, China

Abstract

A Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water is described. This process provides atom-economical access to oxygen-bridged tetrahydro-1,4-oxazepines, where the bridged oxygen atom originates from water. The unique property of the Brønsted acid shows distinct chemoselectivity from the corresponding gold-catalyzed cycloadditions.

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Article information

DOI: https://doi.org/10.1039/C8CC00881G
Article type: Communication
Submitted: 01 Feb 2018
Accepted: 16 Mar 2018
First published: 16 Mar 2018

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Chem. Commun., 2018,54, 3963-3966

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Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines

Y. Zhao, C. Wang, Y. Hu and B. Wan, Chem. Commun., 2018, 54, 3963 DOI: 10.1039/C8CC00881G

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Chemical Communications

Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines†

Abstract

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Brønsted acid-catalyzed formal [5+2+1] cycloaddition of ynamides and isoxazoles with water: access to oxygen-bridged tetrahydro-1,4-oxazepines

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