Issue 13, 2018

The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

Abstract

Catalytic C–C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the catalytic reductive addition of isocyanoacetates to tertiary lactams/amides to produce 5-methoxyoxazoles, including N-heterocyclic substituted oxazoles and sterically hindered amino oxazoles that are difficult to obtain by traditional oxazole-forming Ugi-type reactions. This one-pot procedure involves the Ir-catalysed partial reduction of lactams/amides and the sequential chemoselective addition of the isocyanide group in isocyanoacetates.

Graphical abstract: The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

Supplementary files

Article information

Article type
Research Article
Submitted
26 Mar 2018
Accepted
16 May 2018
First published
17 May 2018

Org. Chem. Front., 2018,5, 2051-2056

The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates

X. Hu, T. Shen, D. Cai, J. Zheng and P. Huang, Org. Chem. Front., 2018, 5, 2051 DOI: 10.1039/C8QO00312B

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