Lewis-Base-Catalyzed
[1 + 2 + 2] Annulation Reaction
of Morita–Baylis–Hillman Carbonates with Unsaturated
Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused
Dispiropyrazolones
The
first Lewis-base-catalyzed unexpected [1 + 2 + 2] annulation
reaction between Morita–Baylis–Hillman carbonates and
unsaturated pyrazolones was developed. The multicyclic cyclopentane-fused
dispiropyrazolone constructions containing five contiguous stereogenic
centers, including two spiro quaternary centers, were prepared with
excellent yields (81–98%) and moderate to good diastereoselectivities
(1:1 to 13:1). Further transformation and gram-scale operations were
also achieved efficiently.