Joshi Harshit, Sathyamoorthi Shyam
Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
J Org Chem. 2022 Apr 1;87(7):5017-5028. doi: 10.1021/acs.joc.2c00119. Epub 2022 Mar 16.
We present protocols for the highly regioselective hydroxyselenylation and silanoxyselenylation of allylic silanols. -(Phenylseleno)phthalimide acts as the selenylating agent for both transformations. Under basic conditions, hydroxyselenylation proceeds with >20:1 regioselectivity, and the products are valuable synthons for further transformations. We show that the silanol plays a critical role in maintaining the yield and regioselectivity of this reaction. Surprisingly, under acidic conditions, the hydroxyselenylation pathway is blocked, and products of a tethered silanoxyselenylation are exclusive.
我们展示了烯丙基硅醇的高度区域选择性羟基硒化和硅氧基硒化的方案。-(苯硒基)邻苯二甲酰亚胺作为两种转化反应的硒化试剂。在碱性条件下，羟基硒化反应以大于20:1的区域选择性进行，其产物是用于进一步转化的有价值的合成子。我们表明硅醇在维持该反应的产率和区域选择性方面起着关键作用。令人惊讶的是，在酸性条件下，羟基硒化途径被阻断，并且唯一得到的是连接的硅氧基硒化产物。
