Issue 2, 2021

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
10 okt 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
Creative Commons BY-NC license

Chem. Sci., 2021,12, 774-779

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

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