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Construction of Polyfunctionalized 6–5–5 Fused Tricyclic Carbocycles via One-Pot Sequential Semipinacol Rearrangement/Michael Addition/Henry Reaction

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posted on 2020-02-24, 22:43 authored by Fu-Ping Zhu, Xiang Guo, Fu-Min Zhang, Xiao-Ming Zhang, Hong Wang, Yong-Qiang Tu
A novel one-pot semipinacol rearrangement/Michael addition/Henry reaction of vinylogous α-ketols with nitroolefins has been achieved through the promotion of two Lewis acids, namely, TMSOTf and TiCl4, at temperatures between 0 and −78 °C. A range of synthetically challenging polyfunctionalized 6–5–5 and 7–5–5 fused tricyclic carbocycles bearing up to five continuous stereocenters, including one quaternary carbon center, are rapidly constructed in moderate to good yields with good to high diastereoselectivities in most cases.

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