jo980987b_si_001.pdf (401.75 kB)
Nickel- and Zinc-Promoted [2 + 2 + 2] Cycloaddition of Diynes and α,β-Enones
journal contribution
posted on 1998-09-09, 00:00 authored by Shin-ichi Ikeda, Hitomi Watanabe, Yoshiro SatoThe [2 + 2 + 2] cycloaddition of diynes and enones occurred in the presence of both nickel and zinc
together. This binary metal-mediated reaction had two interesting features: (1) a terminally
unsubstituted diyne reacted with an enone to give an aromatic compound with the concomitant
incorporation of two hydrogen atoms abstracted from an expected 1,3-diene product into another
molecule of the starting enone and (2) a trimethylsilyl-substituted diyne reacted with an equimolar
amount of enone to regioselectively afford a 1,3-diene, in which the trimethylsilyl group is adjacent
to the carbonyl group.