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A copper catalyzed enantioselective[3+2]annulation of donor-acceptor cyclopropanes with cyclic ke-tones has been developed,providing a concise protocol to enantioenriched 1-oxaspiro[4.5]decanes in up to 98％ yield with up to ＞99/1 dr and up to 92％ee.In addition,this method also provides a facile access to the enantioselective desymmetrisation of various 4-substituted cyclohexanones.The resulting products were easily converted to the core structures of two natural products Heliespirones A and halogenated sesquiterpene isolated from L.saitoi.