Sulfur dioxide (SO₂), as an atmospheric pollutant, has been increasingly attracting the interest of scientists regarding its chemical utilization. Vicinal sulfonyl-functionalization of alkenes through SO₂ insertion offers an innovative method to introduce both sulfonyl and other functional groups into a single molecule. This approach boosts compound diversity while eliminating the need for multi-step operation. On the other hand, the asymmetric construction of quaternary all-carbon stereocenters remains a persistent synthetic challenge. In particular, methods for the synthesis of chiral sulfones bearing an all-carbon quaternary stereocenter are rare. Herein, we present a copper-catalyzed vicinal cyano-arylsulfonylation of acrylamides via the insertion of sulfur dioxide (SO₂), providing an easy way to achieve this goal with minimally functionalized starting materials. The reaction proceeds under mild conditions through a verified single-electron-transfer (SET) mechanism with excellent enantioselectivity (mostly >99% ee), good functional group tolerance, and a broad substrate scope (>50 examples). Notably, this four-component reaction is applicable to the direct chiral functionalization of amino acid and peptide derivatives.

中文翻译：

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从二氧化硫获得具有全碳季立体中心的手性砜


二氧化硫（SO ₂ ）作为一种大气污染物，其化学利用越来越引起科学家的兴趣。通过 SO ₂ 插入对烯烃进行邻位磺酰基官能化提供了一种将磺酰基和其他官能团引入单个分子的创新方法。这种方法提高了化合物的多样性，同时消除了多步骤操作的需要。另一方面，四元全碳立构中心的不对称结构仍然是一个持续存在的合成挑战。特别是，具有全碳四元立构中心的手性砜的合成方法很少见。在此，我们提出了一种通过插入二氧化硫（SO ₂ ）的铜催化丙烯酰胺邻位氰基芳基磺酰化反应，提供了一种使用最少官能化的起始材料实现这一目标的简单方法。该反应在温和的条件下通过经过验证的单电子转移 (SET) 机制进行，具有优异的对映选择性（大部分 >99% ee）、良好的官能团耐受性和广泛的底物范围（>50 个实例）。值得注意的是，这种四组分反应适用于氨基酸和肽衍生物的直接手性官能化。