Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



An Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot to prepare oxazonine-fused endoperoxides

Author affiliations

Abstract

We report a relay catalysis for the highly stereoselective synthesis of densely substituted oxazonine-fused endoperoxides in good yields. This domino reaction is based on an Yb(OTf)3 and visible light promoted [3 + 2] cycloaddition/[3,3]-rearrangement, and in situ [4 + 2] cycloaddition with air in one pot under mild reaction conditions from N-vinyl-α,β-unsaturated nitrones and methylenecyclopropanes, leading to a practical assembly of densely substituted oxazonine-fused endoperoxides containing five stereocenters with a wide substrate scope and excellent diastereoselectivity. Mechanistic studies reveal that the O–O bond of the endoperoxide ring is derived from singlet oxygen (1O2) generated by air under a white LED. Moreover, such an asymmetric relay catalyst has also been realized to afford chiral endoperoxides in good enantioselectivity. Biological tests show that the designed oxazonine-fused endoperoxides significantly inhibited nitric oxide (NO) generation in LPS-stimulated RAW264.7 cells and exhibited their bioactivity as good anti-inflammatory agents.

Graphical abstract: An Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot to prepare oxazonine-fused endoperoxides

Back to tab navigation

Supplementary files

Article information


Submitted
15 Mar 2020
Accepted
04 May 2020
First published
04 May 2020

Green Chem., 2020, Advance Article
Article type
Paper

An Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot to prepare oxazonine-fused endoperoxides

X. Ma, C. Nong, Y. Liang, P. Xu, X. Guo, C. Liang, C. Pan, G. Su and D. Mo, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00929F

Social activity

Search articles by author

Spotlight

Advertisements