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Phosphine-Catalyzed Regio- and Stereo-Selective Hydroboration of Ynamides to (Z)-β-Borylenamides

par Jos, Swetha;Tan, Christine;Thilmany, Pierre ;Saadane, Alaâ ;Slebodnick, Carla;Evano, Gwilherm ;Santos, Webster L.
Référence Chemical communications, 58, page (13751–13754)
Publication Publié, 2022-11-17

Article révisé par les pairs

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Résumé :

We report a tri-n-butyl phosphine catalyzed regio- and stereo-selective hydroboration of ynamides to yield (Z)-β-borylenamides in good yields. Surprisingly, a formal cis addition to the triple bond was observed as confirmed by NMR and X-ray crystallography. 31P NMR studies suggest that a zwitterionic vinylphosphonium intermediate is key in the mechanism. The resulting products were further transformed to β-CF3 enamides via stereoretentive trifluoromethylation.