Constructing chiral bispirooxindoles is difficult to achieve but highly attractive owing to their many potential applications in medicinal chemistry. Here we present an asymmetric [3+2] annulation reaction of Morita–Baylis–Hillman carbonates from isatins and isatin‐based N‐Boc‐ketimines under the catalysis of a newly designed multifunctional 4‐dimethylaminopyridine‐type substance. The reaction shows high γ‐regioselectivity, producing highly complex 1,2‐bispirooxindoles incorporating a dihydropyrrolidine motif in excellent yields with moderate to outstanding stereoselectivity (dr>19:1, up to >99% ee). This protocol has been expanded to utilize trifluoromethyl‐containing ketimines, delivering complicated architectures with fused and spirocyclic frameworks in modest enantioselectivity.

中文翻译：

---

不对称的[3 + 2]环法构建包含二氢吡咯烷基序的1,2-Bispirooxindoles

构造手性双螺硫辛酯很难实现，但由于其在药物化学中的许多潜在应用，因此具有很高的吸引力。在此，我们介绍了在新设计的多功能4-二甲基氨基吡啶类物质的催化下，由靛红和基于靛红的N - Boc-酮亚胺形成的森田-贝利斯-希尔曼碳酸盐的不对称[3 + 2]环化反应。该反应显示出高的γ-区域选择性，可产生具有二氢吡咯烷基序的高度复杂的1,2-双螺并氧杂吲哚类化合物，产率高，立体选择性中等至出色（dr > 19：1，ee > 99％））。该协议已扩展为利用含三氟甲基的酮亚胺，以适度的对映选择性提供具有稠合和螺环骨架的复杂结构。