中央民族大学胡小强团队报道了Peterson烯烃/Michael加成/C(sp³)芳基化级联的六元碳环螺菌吲哚模块化组装。相关研究成果于2024年7月3日发表在国际顶尖学术期刊《中国化学》。

螺环吲哚的简明组装在现代有机合成中具有重要意义，但也是一项具有挑战性的任务。

该文描述了一种罕见的碱促进的[4+2]螺环化很少使用的靛红衍生的β-甲硅烷基甲醇与邻卤芳族酮的反应，这使得能够以高产率快速和模块化地合成六元碳环螺氧吲哚，并具有优异的官能团耐受性（>50个实例）。

机理实验表明，该反应涉及Peterson加成、Michael加成和分子内C（sp3）芳基化级联反应。目标产物的多样化合成衍生化和生物活性分子的成功构建，进一步说明了螺环吲哚相关药物发现的合成潜力。

附：英文原文

Title: Modular Assembly of Six-Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade

Author: Feng-Cheng Jia, Zi-Yi Yuan, Na Luo, Shuang-Xi Gu, Xiao-Qiang Hu

Issue&Volume: 2024-07-03

Abstract: Concise assembly of spirooxindoles is of great significance but a challenging task in modern organic synthesis. Described herein is an unusual base-promoted [4+2] spiroannulation of rarely used isatin-derived β-silylcarbinols with o-halogen aromatic ketones, which enables rapid and modular synthesis of six-membered carbocyclic spirooxindoles in high yields with excellent functional group tolerance (>50 examples). Mechanistic experiments revealed that this reaction involved a Peterson olefination, Michael addition and intramolecular C(sp3) arylation cascade. The variegated synthetic derivatization of target products and successful construction of bioactive molecules further illustrate the synthetic potential in spirooxindole-related drug discovery.

DOI: 10.1002/cjoc.202400410

Source: https://onlinelibrary.wiley.com/doi/full/10.1002/cjoc.202400410