I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

Xia Wu; Xiao Geng; Peng Zhao; Jingjing Zhang; Yan-dong Wu; An-xin Wu

doi:10.1039/C6CC10275A

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I₂-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles†

Xia Wu,^a Xiao Geng,^a Peng Zhao,^a Jingjing Zhang,^a Yan-dong Wu

*^a and An-xin Wu*^a

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* Corresponding authors

^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Hubei, Wuhan 430079, P. R. China
E-mail: chwuyd@mail.ccnu.edu.cn, chwuax@mail.ccnu.edu.cn

Abstract

An I₂-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the C [triple bond, length as m-dash] N cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

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Article information

DOI: https://doi.org/10.1039/C6CC10275A
Article type: Communication
Submitted: 28 Dec 2016
Accepted: 28 Feb 2017
First published: 28 Feb 2017

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Chem. Commun., 2017,53, 3438-3441

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I₂-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles

X. Wu, X. Geng, P. Zhao, J. Zhang, Y. Wu and A. Wu, Chem. Commun., 2017, 53, 3438 DOI: 10.1039/C6CC10275A

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