Issue 17, 2018

Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals

Abstract

A one-pot three-component route towards fluorinated five/five-annulated nitroso acetals bearing two fused isoxazolidine rings is described. Target nitroso acetals were obtained with complete regioselectivity and high stereoselectivity. The mechanism of this tandem [4 + 1]/[3 + 2] cycloaddition was proposed to include the intermediate formation of elusive 3-fluoro-isoxazoline-N-oxides as key intermediates. This method is applicable for the synthesis of a broad scope of nitroso acetals starting from various fluoronitroalkenes, halogenated dicarbonyl compounds and dipolarophiles of different electronic nature.

Graphical abstract: Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals

Supplementary files

Article information

Article type
Research Article
Submitted
25 Jun 2018
Accepted
31 Jul 2018
First published
31 Jul 2018

Org. Chem. Front., 2018,5, 2588-2594

Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: one-pot three-component assembly of fluorinated bicyclic nitroso acetals

V. A. Motornov, A. A. Tabolin, R. A. Novikov, Y. V. Nelyubina, V. G. Nenajdenko and S. L. Ioffe, Org. Chem. Front., 2018, 5, 2588 DOI: 10.1039/C8QO00623G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements