Issue 42, 2019

Chemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event

Abstract

Aliphatic C–H functionalization is a topic of current intense interest in organic synthesis. Herein, we report that a facile and stereoselective dehydrogenation event enables the functionalization of aliphatic amides at different positions in a one-pot fashion. Derivatives of relevant pharmaceuticals were formally functionalized in the β-position in late-stage manner. A single-step synthesis of incrustoporine from a simple precursor further showcases the potential utility of this approach.

Graphical abstract: Chemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event

Supplementary files

Article information

Article type
Edge Article
Submitted
28 Jul 2019
Accepted
29 Aug 2019
First published
10 Sep 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 9836-9840

Chemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event

A. Bauer and N. Maulide, Chem. Sci., 2019, 10, 9836 DOI: 10.1039/C9SC03715B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements