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Chemoselective formal ?-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 ?-position in late-stage manner. A single-step synthesis of incrustoporine from a simple precursor further showcases the potential utility of this approach.

SUBMITTER: Bauer A

PROVIDER: S-EPMC6977552 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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

Bauer Adriano A Maulide Nuno N

Chemical science 20190910 42

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. ...[more]

PMID: 32015806

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