Next, a series of cyclic silyl enol ethers derived from 5-, 6-, 7-membered cyclic ketones including those fused with aromatic-and heteroaromatic rings were assessed, producing the corresponding assortment of bridged polycycles (3adan) in synthetically useful yields. Interestingly, these reactions could convert cyclic silyl dienol ethers to tricyclic alkenes 3al and 3am, which are suitable for further elaborations to synthesize more complex molecular frameworks. Notably, acyclic tri-and tetra-substituted silyl enol ethers are viable substrates, allowing the rapid construction of highly substituted and compact bicycles 3ao-aq. It is worth noting that the reaction with different trisubstituted silyl enol ethers resulted in distinct diastereoselectivities. In particular, 3ao were obtained in high diastereoselectivity (13:1 dr) from corresponding silyl enol ether 1ao (Z/E = 10:1) derived from 1-phenyl-1-butanone, while 3ap was formed as a mixture of diastereomers (1.3:1 dr) with silyl enol ether 1ap (Z/E = 7.4:1) derived from 3-pentanone (see the supporting information for details).