Rapid Access to γ-Amino-α-aryl Alcohol Scaffolds via an Enamine-Based Heck Coupling
作者:Bowen Li、Gregory P. Tochtrop
DOI:10.1021/acs.joc.1c03056
日期:2022.3.4
inhibitors directed toward a critical family of metabolic enzymes. Here we report the transformation of simple aryl halides to a highly functionalized benzyl (3-oxo-3-arylpropyl)carbamate intermediate that can rapidly be converted to a high value γ-amino-α-aryl alcohol. This chemistry is realized through a two-step process involving an enamine-based Heck coupling (EBHC) followed by a one-pot catalytic
γ-氨基-α-芳基醇是设计针对关键代谢酶家族的抑制剂的关键官能团。在这里,我们报告了将简单的芳基卤化物转化为高度官能化的苄基 (3-氧代-3-芳丙基) 氨基甲酸酯中间体,该中间体可以快速转化为高价值的 γ-氨基-α-芳基醇。这种化学反应是通过一个两步过程实现的,包括基于烯胺的 Heck 偶联 (EBHC),然后是一锅催化 Cbz 脱保护和 EBHC 产物的酮还原。