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Chem Commun (Camb). 2018 Jul 03;54(54):7435-7438. doi: 10.1039/c8cc03140a.

Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration.

Chemical communications (Cambridge, England)

Xin-Qi Zhu, Qing Sun, Zhi-Xin Zhang, Bo Zhou, Pei-Xi Xie, Wen-Bo Shen, Xin Lu, Jin-Mei Zhou, Long-Wu Ye

Affiliations

  1. iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China. [email protected].

PMID: 29789833 DOI: 10.1039/c8cc03140a

Abstract

A novel zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration has been developed, which represents the first example of a non-noble metal-catalyzed reaction between isoxazoles and alkynes. This method allows the facile and atom-economical synthesis of a range of valuable β-keto enamides. Moreover, the computational study provides further evidence for the feasibility of the proposed reaction mechanism.

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