Neighboring phenolic group-activated gem-difluoroallylboration of imines for the catalyst-free synthesis of gem-difluorohomoallylamines
Neighboring phenolic group-activated gem-difluoroallylboration of imines for the catalyst-free synthesis of gem-difluorohomoallylamines
复制标题
邻近酚基团激活的亚胺偕二氟烯丙基硼化反应用于无催化剂合成偕二氟高烯丙胺
DOI：
10.1039/c8ob00541a
复制
发表时间：
2018
影响因子：
3.2
通讯作者：
Huang Yi-Yong
中科院分区：
文献类型：
--
作者：
Yang Xing;Zhang Feng;Zhou Yang;Huang Yi-Yong
我们在此报告了频哪醇偕二氟烯丙硼酸酯和亚胺在无催化剂条件下由N-保护基团中的相邻酚基团实现的前所未有的加成反应，从而促进了多种外消旋偕二氟高烯丙胺衍生物的构建。基于对照实验，通过 Zimmerman-Traxler 模型提出了一个合理的过渡态，以阐明邻近酚基的重要性以及硼酸酯试剂的 γ-选择性。
We herein report an unprecedented addition reaction of pinacol gem-difluoroallylborates and imines enabled by a neighboring phenolic group in an N-protecting group under catalyst-free conditions, thus facilitating the construction of a wide range of racemic gem-difluorohomoallylamine derivatives. Based on the control experiments, a plausible transition state via the Zimmerman–Traxler model was proposed to elucidate the significance of the neighboring phenolic group, as well as the γ-selectivity of the boronate reagents.