Synthesis of 3-Acyl-isoxazoles and Δ²-Isoxazolines from Methyl Ketones, Alkynes or Alkenes, and tert-Butyl Nitrite via a Csp³-H Radical Functionalization/Cycloaddition Cascade

Peng Dai, Xin Tan, Qian Luo, Xiang Yu, Shuguang Zhang, Fang Liu*, Wei-Hua Zhang*

*Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China, Email: acialiunjau.edu.cn, njzhangwh126.com

P. Dai, X. Tan, Q. Luo, X. Yu, S. Zhang, F. Liu, W.-H. Zhang, Org. Lett., 2019, 21, 5096-5100.

DOI: 10.1021/acs.orglett.9b01683

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Abstract

A metal-free Csp³-H bond functionalization of ketones with tert-butyl nitrite followed by a 1,3-dipolar cycloaddition to alkynes or alkenes provides oxazole and isoxazoline derivatives with diverse functionalities.

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Key Words

isoxazoles

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ID: J54-Y2019