A base promoted formal [4+1] cycloaddition of ortho- and para-quinone methides with 3-chlorooxindoles is reported to afford various functionalized 3,2’-tetrahydrofuryl spirooxindoles with an unexpected reversal diastereoselectivity. Different configurations of 1,4-addition and 1,6-addition at the oxindole carbanionic center are found to the origin of diastereoselection through DFT calculations. These structurally unique spirooxindole derivatives show promising anti-tumor activity.

中文翻译：

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邻-或对-醌甲基与 3-氯氧吲哚的正式 [4+1] 环化：合成 3,2'-四氢呋喃螺氧吲哚

据报道，碱促进了邻- 和对 -醌甲基化物与 3-氯代吲哚的正式 [4+1] 环加成反应，以提供各种功能化的 3,2'-四氢呋喃基螺吲哚，并具有意想不到的逆转非对映选择性。通过 DFT 计算，发现 oxindole 碳负离子中心的 1,4-加成和 1,6-加成的不同构型是非对映选择的起源。这些结构独特的螺吲哚衍生物显示出有希望的抗肿瘤活性。