Organic Chemistry

A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

Authors

Abstract

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

Content

Thumbnail image of Manuscript.pdf

Supplementary material

Thumbnail image of Supporting Info.pdf
Supporting Info
Thumbnail image of 3u.txt
3u