Highly functionalized cyclopentenones have been prepared stereospecifically through a chemoselective copper(II)-mediated Nazarov/Wagner–Meerwein rearrangement sequence. After the initial 4π electrocyclization, this reaction involves two sequential [1,2]-migrations depending upon both migratory ability and steric bulk of the substituents at C1 and C5 (see scheme). The proposed mechanism of the reaction is supported by DFT studies.
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