Organic Letters
Organic Letters
5 years ago

Fluorinated Amine Stereotriads via Allene Amination

Fluorinated Amine Stereotriads via Allene Amination
Lu Liu, Nels C. Gerstner, Jennifer M. Schomaker, Lucas J. Oxtoby, Ilia A. Guzei
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 α-, β-, and γ-amino acids.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01342

DOI: 10.1021/acs.orglett.7b01342

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