Cyclic sulfones from double conjugate addition of Rongalite
Cyclic sulfones from double conjugate addition of Rongalite
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DOI：
10.1080/00397911.2023.2222316
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发表时间：
2023-06
影响因子：
2.1
通讯作者：
Melina Goga;Haonan Zong;Jazmine Prana;Rudolph Michel;Antonia Muro;Elana Rubin;Janet Brenya;M. Bebbington
中科院分区：
文献类型：
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作者：
Melina Goga;Haonan Zong;Jazmine Prana;Rudolph Michel;Antonia Muro;Elana Rubin;Janet Brenya;M. Bebbington
摘要 通过将雕白粉（羟甲基亚磺酸钠）与二烯酮进行双共轭加成，可以得到环状砜，收率高达 92%。每种情况下的主要产物是3,5-二取代酮砜的动力学反式异构体。报道了十一个例子，包括芳基和烷基取代的底物。该方法的优点是实验简单、对质子和氧化敏感官能团的耐受性以及具有空间挑战性的底物。这项工作还显着扩展了雕白粉作为共轭亲核试剂的范围。图解摘要
Abstract Cyclic sulfones are obtained in up to 92% yield by double conjugate addition of Rongalite (sodium hydroxymethyl sulfinate) to dienones. The major product in each case is the kinetic trans-isomer of the 3,5-disubstituted ketosulfone. Eleven examples, including aryl and alkyl substituted substrates, are reported. The advantages of the method are its experimental simplicity, tolerance for both protic and oxidation-sensitive functional groups, and sterically challenging substrates. The work also significantly expands the scope of Rongalite as a conjugate nucleophile. Graphical Abstract