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We have established Lewis acid-catalyzed allylation, cyanation and azidation of 1,4-disubstituted 1,4-epoxy-1,4-dihydronaphthalenes to afford the corresponding unique and multi-functionalized naphthalene derivatives.These methodologies enable excellent regioselective functionalizations of unsymmetrical substrates containing electron-donationg groups (R3 and R4) on the aromatic ring or aryl group (R1) at the bridgehead.