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Fluorinated Amine Stereotriads via Allene Amination.

ABSTRACT: The incorporation of fluorine into organic scaffolds often improves the bioactivity of pharmaceutically relevant compounds. C-F/C-N/C-O stereotriad motifs are prevalent in antivirals, neuraminidase inhibitors, and modulators of androgen receptors, but are challenging to install. An oxidative allene amination strategy using Selectfluor rapidly delivers triply functionalized triads of the form C-F/C-N/C-O, exhibiting good scope and diastereoselectivity for all syn products. The resulting stereotriads are readily transformed into fluorinated pyrrolidines and protected ?-, ?-, and ?-amino acids.

SUBMITTER: Liu L

PROVIDER: S-EPMC5541934 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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Fluorinated Amine Stereotriads via Allene Amination.

Liu Lu L Gerstner Nels C NC Oxtoby Lucas J LJ Guzei Ilia A IA Schomaker Jennifer M JM

Organic letters 20170602 12

The incorporation of fluorine into organic scaffolds often improves the bioactivity of pharmaceutically relevant compounds. C-F/C-N/C-O stereotriad motifs are prevalent in antivirals, neuraminidase inhibitors, and modulators of androgen receptors, but are challenging to install. An oxidative allene amination strategy using Selectfluor rapidly delivers triply functionalized triads of the form C-F/C-N/C-O, exhibiting good scope and diastereoselectivity for all syn products. The resulting stereotri ...[more]

PMID: 28573862

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