Facile allylboration of ketones with β-benzyloxy-γ,γ-difluoroallylboronate: Preparation of gem-difluorinated homoallylic tert-alcohols

The reaction of β-benzyloxy-γ,γ-difluoroallylboronate, at room temperature and in the absence of catalysts, with a variety of aromatic and aliphatic ketones of varying sterics and electronic requirements furnishes fluorinated homoallylic tert-alcohols in 62–82% yields. Representatives of these alcohols were converted to their corresponding α,α-difluoro-β-hydroxy ketones in 73–85% yields.

Graphical abstractThe reaction of β-benzyloxy-γ,γ-difluoroallylboronate, at room temperature and in the absence of catalysts, with a variety of aromatic and aliphatic ketones of varying sterics and electronic requirements furnishes fluorinated homoallylic tert-alcohols in 62–82% yields. Representatives of these alcohols were converted to their corresponding α,α-difluoro-β-hydroxy ketones in 73–85% yields.Figure optionsDownload full-size imageDownload as PowerPoint slide