An open-close strategy in asymmetric catalysis is newly developed. With this powerful strategy, lactols are directly applied as potential precursors of lactones in enamine-based asymmetric Michael reactions providing a facile access to α-functionalized lactones containing two adjacent stereogenic centers as a single diastereomer in good to excellent yields (up to 99%) and with excellent enantioselectivities (most cases >99%). Moreover, the reaction products are shown to give highly functionalized derivatives by stepwise systematic transformations.