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Regio-reversed domino processes of triketone enones with azlactones have been established. Opposite to the previous β-addition-triggered domino processes, this protocol is initiated by a regio-reversed α-addition. Under catalyst-free conditions, the domino reaction readily occurred, leading to the formation of a variety of bicyclic furofurans bearing vicinal quaternary carbons in good to excellent yields. In addition, a catalytic asymmetric version was achieved using chiral phosphoric acid catalysis, in which H2O played a crucial role in enantio-control. Notably, all the prepared enantio-enriched products could be further recrystallized to ensure excellent enantioselectivity. [ABSTRACT FROM AUTHOR]