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A copper-catalyzed diastereoselective O-transfer reaction of N-vinyl-α,β-unsaturated nitrones with ketenes into γ-lactones through [5 + 2] cycloaddition and N–O bond cleavage

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Abstract

A general protocol for the construction of novel densely functionalized γ-lactones was developed in good to excellent yields with high diastereoselectivity from easily available N-vinyl-α,β-unsaturated nitrones and ketenes. The reaction involves copper-catalyzed [5 + 2] cycloaddition, N–O bond cleavage, 6π electron cyclization, and aromatization to afford various γ-(pyridin-2-yl)lactones over four step transformations in a single flask. The present method features mild reaction conditions, high atom economy, high regio- and diastereoselectivity, diversity of γ-lactones, and a new application of the O-transfer reaction.

Graphical abstract: A copper-catalyzed diastereoselective O-transfer reaction of N-vinyl-α,β-unsaturated nitrones with ketenes into γ-lactones through [5 + 2] cycloaddition and N–O bond cleavage

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Publication details

The article was received on 31 May 2019, accepted on 22 Sep 2019 and first published on 24 Sep 2019


Article type: Communication
DOI: 10.1039/C9GC01811E
Green Chem., 2019, Advance Article

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    A copper-catalyzed diastereoselective O-transfer reaction of N-vinyl-α,β-unsaturated nitrones with ketenes into γ-lactones through [5 + 2] cycloaddition and N–O bond cleavage

    J. Liao, Q. Wu, X. Lu, N. Zou, C. Pan, C. Liang, G. Su and D. Mo, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC01811E

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