Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur
作者:Masato Saito、Sho Murakami、Takeshi Nanjo、Yusuke Kobayashi、Yoshiji Takemoto
DOI:10.1021/jacs.0c03256
日期:2020.5.6
for the thioacylation of amines using α-ketoacids and elemental sulfur has been developed. The key to success for this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties are tolerated under the applied reaction conditions. To demonstrate
已经开发了一种使用 α-酮酸和元素硫对胺进行硫代酰化的温和且化学选择性的方法。这种转化成功的关键是硫醇(如 1-十二烷硫醇)对元素硫的亲核活化。在所应用的反应条件下,可以耐受各种官能团,包括未保护的羟基、羧基、酰胺、硫化物和叔胺部分。为了证明与使用 Lawesson 试剂或 P2S5 的传统 OS 交换反应相比,该方法的优势,将硫代酰胺部分特定地引入到生物活性化合物中。