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Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita–Baylis–Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones

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posted on 18.09.2018, 00:00 authored by Jin-Yan Liang, Shou-Jie Shen, Xiao-Qian Chai, Ting Lv
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.