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

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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

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Publication details

The article was received on 28 Jul 2019, accepted on 29 Aug 2019 and first published on 10 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03715B
Chem. Sci., 2019, Advance Article
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    Chemoselective formal β-functionalization of substituted aliphatic amides enabled by a facile stereoselective oxidation event

    A. Bauer and N. Maulide, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03715B

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