Jump to main content
Jump to site search

Issue 2, 2021
Previous Article Next Article

Acyclic nitronate olefin cycloaddition (ANOC): regio- and stereospecific synthesis of isoxazolines

Author affiliations

Abstract

We report the first demonstrations of intra- and intermolecular acyclic nitronate olefin cycloaddition (ANOC) reactions that enable the highly efficient syntheses of isoxazolines bearing various functional groups. This general approach to accessing γ-lactone fused isoxazolines was hitherto unprecedented. The room temperature transformations reported herein exhibit wide substrate scopes, as evidenced by more than 70 examples, including the generation of five tricyclic isoxazolines. The robustness of this methodology was confirmed by a series of trials that afforded highly functionalized isoxazolines. Both experimental results and density functional theory calculations indicate that these transformations proceed via the in situ formation of acyclic nitronates together with concerted [3+2] cycloaddition and tert-butyloxy group elimination processes to give regio- and stereospecificity.

Graphical abstract: Acyclic nitronate olefin cycloaddition (ANOC): regio- and stereospecific synthesis of isoxazolines

Back to tab navigation

Supplementary files

Article information


Submitted
10 Oct 2020
Accepted
06 Nov 2020
First published
06 Nov 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 774-779
Article type
Edge Article

Acyclic nitronate olefin cycloaddition (ANOC): regio- and stereospecific synthesis of isoxazolines

L. Ma, L. Kou, F. Jin, X. Cheng, S. Tao, G. Jiang, X. Bao and X. Wan, Chem. Sci., 2021, 12, 774
DOI: 10.1039/D0SC05607C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material and it is not used for commercial purposes.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.


Social activity

Search articles by author

Spotlight

Advertisements