Issue 14, 2021

N-Alkyl nitrones as substrates for access to N-aryl isoxazolidines via a catalyst-free one-pot three-component reaction with nitroso compounds and olefins

Abstract

N-Alkyl nitrones are used as the starting materials to construct various N-aryl isoxazolidines, instead of N-alkyl isoxazolidines or N–H 1,3-oxazinanes via a catalyst-free one-pot three-component reaction with nitroso compounds and olefins. The mechanism investigations indicate that the in situ formation of N-aryl nitrones from the reaction of N-alkyl nitrones and nitrosoarenes is the key step. The protocol features broad substrate scope, good to excellent chemo-, regio- and diastereo-selectivities, and moderate to excellent yields for most substrates.

Graphical abstract: N-Alkyl nitrones as substrates for access to N-aryl isoxazolidines via a catalyst-free one-pot three-component reaction with nitroso compounds and olefins

Supplementary files

Article information

Article type
Research Article
Submitted
11 Mar 2021
Accepted
04 May 2021
First published
07 May 2021

Org. Chem. Front., 2021,8, 3752-3759

N-Alkyl nitrones as substrates for access to N-aryl isoxazolidines via a catalyst-free one-pot three-component reaction with nitroso compounds and olefins

P. Zhai, W. Li, J. Lin, S. Huang, W. Gao and X. Li, Org. Chem. Front., 2021, 8, 3752 DOI: 10.1039/D1QO00398D

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