Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation
Oxygen-to-Oxygen Silyl Migration of α-Siloxy Sulfoxides and Oxidation-Triggered Allicin Formation
复制标题
α-甲硅烷氧基亚砜的氧到氧甲硅烷基迁移和氧化引发的大蒜素形成
DOI：
10.1021/acs.orglett.1c01149
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Xian, Ming
中科院分区：
文献类型：
--
作者：
Kelly, Shane S.;Shen, Tun-Li;Xian, Ming
α-甲硅烷氧基硫醚的氧化导致作为不稳定中间体的相应亚砜的形成，其经历分子内氧到氧甲硅烷基的迁移以破坏C-S键。该方法产生甲硅烷基保护的次磺酸和随后的硫代亚磺酸酯。它被用于开发氧化触发的大蒜素供体。
Oxidation of α-siloxy thioethers leads to the formation of the corresponding sulfoxides as unstable intermediates, which undergo an intramolecular oxygen-to-oxygen silyl migration to break the C–S linkage. This process produces silyl protected sulfenic acids and subsequently thiosulfinates. It was used to develop oxidation-triggered allicin donors.