Journal of the American Chemical Society, Vol.133, No.32, 12454-12457, 2011
Conjugate Addition-Initiated Nazarov Cyclization
A reaction sequence involving the 1,6-conjugate addition of a nucleophile to a dienyl diketone followed by Nazarov cyclization is described. Several nucleophiles are identified as competent initiators for the sequence. A different reaction outcome is observed when catalytic amounts of nucleophile are employed, involving elimination of the nucleophile after the electrocyclization.