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Ynones are a unique class of structural motifs that show remarkable chemical versatility. Chiral ynones, particularly those possessing an alpha-stereogenic center, are highly attractive templates for structural diversification. So far, only very limited examples have been reported for asymmetric alpha-functionalization of ynones. Asymmetric double alpha-functionalization of ynones remains elusive. Here we describe a streamlined strategy for asymmetric alpha-difunctionalization of ynones. We developed a gold-catalyzed multicomponent condensation reaction from a simple ynone, an amine, and an electrophilic alkynylating reagent to generate a 1,2-dialkynyl enamine, a key stable and isolable intermediate. This intermediate can undergo asymmetric fluorination catalyzed by a chiral phosphoric acid derivative. Chiral ynones with an alpha-quaternary carbon and containing a fluorine and an alkyne can be synthesized in high yield and high ee. The synthetic utility of this method is demonstrated by the synthesis of enantioenriched tri(hetero) arylmethyl fluorides