Copper- and Borinic Acid-catalyzed Propargylic Etherification of Propargylic Carbonates with Benzyl Alcohols
Copper- and Borinic Acid-catalyzed Propargylic Etherification of Propargylic Carbonates with Benzyl Alcohols
复制标题
DOI：
10.1246/cl.180123
复制
发表时间：
2018-03
影响因子：
1.6
通讯作者：
K. Tsuchida;M. Yuki;K. Nakajima;Y. Nishibayashi
中科院分区：
文献类型：
--
作者：
K. Tsuchida;M. Yuki;K. Nakajima;Y. Nishibayashi
炔丙基取代反应提供了有用的合成方法，因为基于炔丙基取代产物中的炔部分的进一步转化容易实现以构建更复杂的有机化合物。大量的工作致力于各种亲核试剂与炔丙基的不对称取代反应。然而，迄今为止，使用醇作为亲核试剂的成功例子相当有限。为了实现脂肪醇的利用，本文中我们报告了使用铜-pybox络合物和硼酸的组合催化。在该催化体系中，苯甲醇衍生物等脂肪醇类化合物成功地应用于炔丙基醚化反应，得到了高产率、高对映选择性的炔丙基醚化产物。
Propargylic substitution reactions have offered useful synthetic methods because further transformations based on the alkyne moiety in the propargylic substituted products was readily achieved to construct more complex organic compounds. A large number of works have been devoted to enantioselective propargylic substitution reactions with a variety of nucleophiles. However, successful examples of the use of alcohols as nucleophiles have been quite limited until now. To achieve utilization of aliphatic alcohols, herein we report the use of combined catalysis of a copper-pybox complex and a borinic acid. In this catalytic system, aliphatic alcohols such as benzyl alcohol derivatives were successfully applied to afford the corresponding propargylic etherified products in good yields with high enantioselectivities.