Department of Chemistry, Center for Excellence in Molecular Synthesis, Hefei National Laboratory for Physical Science at the Microscale, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 20237, P. R. China.
Org Biomol Chem. 2019 Feb 13;17(7):1901-1905. doi: 10.1039/c8ob02141d.
In this protocol we described a boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles. This diastereo- and enantiospecific reaction provides an efficient entry to prepare a variety of hydroxyl sulfides. Through the directing effect of the hydroxyl group, nucleophilic attack on the C-3 position of the epoxide moiety is favoured. It can be rationalized in a proposed transition state, in which the boronic acid catalyst tethers both epoxides and S-nucleophiles.
在本方案中，我们描述了硼酸催化的 3,4-环氧醇与巯基苯和硫醇作为亲核试剂的 C-3 选择性开环反应。这种非对映选择性和对映选择性的反应为制备各种羟基硫化物提供了有效的途径。通过羟基的导向作用，有利于亲核试剂进攻环氧部分的 C-3 位。这可以在提出的过渡态中得到合理化，其中硼酸催化剂连接两个环氧和 S-亲核试剂。
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