We have developed an efficient and mild enantioselective palladium-catalyzed (5+3) cycloaddition of vinylcyclopropanes and oxidopyrylium ylides generated in situ from benzopyranones, in the presence of a chiral PHOX ligand. These reactions afford various highly functionalized bridged oxa-[3.3.1]carbocycles with three stereogenic centers that are challenging to synthesize, in moderate to good yields and enantioselectivities.
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