Organocatalytic Enantioselective Conjugate Alkynylation of β-Aminoenones: Access to Chiral β-Alkynyl-β-Amino Carbonyl Derivatives.

Readily available potassium alkynyltrifluoroborates were used for organocatalytic asymmetric conjugate alkynylation of β-enaminones. The interception of a modified binaphthol catalyst and in situ generated organodifluoroboranes proved important to access functionalized β-alkynyl-β-amino carbonyls and derivatives with improved chemo-reactivity and enantio-induction. Mechanistic studies revealed the impact of molecular sieves on efficiency and stereocontrol. The products undergo additional functionalization to yield a diverse set of valuable β-alkynyl-β-amino carbonyl scaffolds.