A domino [3 + 2] cycloaddition/deamination/imine hydrolysis reaction of D–A cyclopropane with inexpensive thiourea catalyzed by Lu(OTf)₃ has been developed. A series of γ-thiolactone spirooxindole compounds with potential biological activity were obtained in up to 98% yields. Experiments to investigate the mechanism showed that γ-thiolactone products were from the hydrolysis of the imine intermediates. In addition, the asymmetric catalytic reaction of D–A cyclopropane and thiourea has been successfully developed to afford spiro-γ-thiolactone compounds with good enantioselectivities (up to 98% ee). The utility of this method was showcased by the facile transformation and biological activity of products.

中文翻译：

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环丙基螺吲哚与硫脲的多米诺[3 + 2]环加成/脱氨/亚胺水解反应得到螺-γ-硫代内酯吲哚


开发了 Lu(OTf) ₃ 催化的 D-A 环丙烷与廉价硫脲的多米诺 [3 + 2] 环加成/脱氨/亚胺水解反应。获得了一系列具有潜在生物活性的γ-硫代内酯螺吲哚化合物，收率高达98%。机理实验表明，γ-硫代内酯产物来自于亚胺中间体的水解。此外，D-A环丙烷与硫脲的不对称催化反应已成功开发，可得到具有良好对映选择性（高达98% ee）的螺-γ-硫内酯化合物。该方法的实用性通过产物的简便转化和生物活性得到体现。