Issue 25, 2018

In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

Abstract

Herein, we present a novel [3 + 2] cycloaddition reaction of β-keto esters with nitrile oxides, which were generated in situ from copper carbene and tert-butyl nitrite. This three-component reaction provides new methodology for the direct synthesis of fully substituted isoxazole derivatives, featuring mild reaction conditions, readily accessible starting materials and simple operation. The experimental studies and DFT calculations suggest that the reaction starts with the generation of the key intermediate nitrile oxides, followed by a [3 + 2] cycloaddition reaction of β-keto esters to give the final isoxazole products.

Graphical abstract: In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

Supplementary files

Article information

Article type
Paper
Submitted
08 May 2018
Accepted
03 Jun 2018
First published
04 Jun 2018

Org. Biomol. Chem., 2018,16, 4683-4687

In situ generation of nitrile oxides from copper carbene and tert-butyl nitrite: synthesis of fully substituted isoxazoles

R. Chen, A. A. Ogunlana, S. Fang, W. Long, H. Sun, X. Bao and X. Wan, Org. Biomol. Chem., 2018, 16, 4683 DOI: 10.1039/C8OB01067F

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