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Download fileLewis-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 2018-09-18, 00:00 authored by Jin-Yan Liang, Shou-Jie Shen, Xiao-Qian Chai, Ting LvThe
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.
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spiro quaternary centerscarbonatesLewis-Base-CatalyzedAnnulationCarbonateUnsaturated PyrazolonesannulationdiastereoselectivitietransformationLewis-base-catalyzedmulticyclic cyclopentane-fused dispiropyrazolone constructionsAll-Stereogenic Carbon Cyclopentane-Fused DispiropyrazolonesConstructionstereogenic centersyieldMoritagram-scale operations