Diastereoselective synthesis of spiropyrazolones via 1,3-dipolar [3+2] cycloadditions between pyrazolone-based olefins and N, N’-cyclic azomethine imines
Keyword(s):
X Ray
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Under the catalysis of PhCO2H, the 1,3-dipolar [3+2] cycloaddition between pyrazolone-based olefins and N, N’-cyclic azomethine imines proceeded readily, thus delivering structurally novel spiropyrazolones with up to 98% yield and >20:1 dr. The relative stereochemical configuration of the obtained spiropyrazolones was unambiguously assigned by X-ray single crystal structure analysis. The diastereoselective formation of the title spiropyrazolones was interpreted by the hypothesized reaction mechanism.
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