Sephton Thomas, Liu Zi, Greaney Michael F
School of Chemistry, University of Manchester, Manchester, M13 9PL, UK.
Angew Chem Int Ed Engl. 2025 Sep 15;64(38):e202512577. doi: 10.1002/anie.202512577. Epub 2025 Jul 31.
We describe a triple C─C bond cascade process for heteroaryl cyclopropane synthesis, through the reaction of vinyl sulfonium salts and sulfones under mild conditions. An initial conjugate addition (C─C bond 1) sets up a Smiles-Truce rearrangement (C─C bond 2), with a final 3-exo-tet ring closure (C─C bond 3) affording cyclopropanes. Serendipitously, we uncovered a novel reaction variant that affords sultines, an under-explored heterocycle with potential application as a bioisostere in medicinal chemistry.
我们描述了一种用于合成杂芳基环丙烷的三碳-碳键级联过程，该过程通过乙烯基锍盐和砜在温和条件下的反应实现。初始的共轭加成（碳-碳键1）引发了斯迈尔斯-特鲁斯重排（碳-碳键2），最终通过3-外向-四环化反应（碳-碳键3）生成环丙烷。意外的是，我们发现了一种新型反应变体，该变体可生成环丁砜，这是一种研究较少的杂环化合物，在药物化学中作为生物电子等排体具有潜在应用价值。
