Yang Shan, Chen Yasu, Zhu Chen
Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, State Key Laboratory of Synergistic Chem-Bio Synthesis, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 China
Chem Sci. 2025 Apr 29. doi: 10.1039/d5sc02555a.
Spirocyclic vinyl sulfones, which incorporate the three-dimensional structure inherent to spiro compounds and the Michael acceptor reactivity associated with vinyl sulfones, hold promise for novel biological activities. The lack of efficient synthetic methods, however, hinders their extensive investigations in drug discovery and development. In this work, we describe a practical and versatile approach for the synthesis of multi-functionalized spirocyclic vinyl sulfones from easily available materials. The reaction proceeds efficiently through a cascade of radical cyclization followed by (hetero)aryl migration. The protocol features mild photocatalytic conditions and provides access to a diverse range of products, enabling the construction of complex scaffolds, including medium-sized ring-fused spirocyclic vinyl sulfones.
螺环乙烯基砜结合了螺环化合物固有的三维结构以及与乙烯基砜相关的迈克尔受体反应性，具有产生新型生物活性的潜力。然而，缺乏有效的合成方法阻碍了它们在药物发现和开发中的广泛研究。在这项工作中，我们描述了一种从容易获得的原料合成多功能化螺环乙烯基砜的实用且通用的方法。该反应通过自由基环化级联反应随后进行（杂）芳基迁移而高效进行。该方案具有温和的光催化条件，并能得到多种产物，能够构建复杂的骨架，包括中环稠合的螺环乙烯基砜。
