当前位置:科学网首页 > 小柯机器人 >详情
钯/手性冰片烯协同催化叔苯甲醇的动力学拆分
作者:小柯机器人 发布时间:2021/4/4 23:01:13

武汉大学周强辉团队报道了钯/手性冰片烯协同催化叔苯甲醇的动力学拆分。 相关研究成果于2021年3月30日发表于国际一流学术期刊《德国应用化学》。

该文报道了钯/手性冰片烯协同催化对叔苯甲醇的高对映选择性动力学拆分。以简单的芳基碘为拆分剂,可得到多种外消旋叔苄醇。手性叔苄醇和苯并[c]铬烯产物都具有良好的对映选择性(选择性系数高达544)。

研究人员通过简单制备几种有价值的手性杂环化合物,证明了所得对映体富集叔醇的诱人的合成用途。初步的机理研究包括DFT计算来解释对映体鉴别的起源,以及控制实验来揭示在动力学拆分步骤中瞬时轴向手性的形成。

附:英文原文

Title: Kinetic Resolution of Tertiary Benzyl Alcohols via Palladium/Chiral Norbornene Cooperative Catalysis

Author: Qianghui Zhou, Yu Hua, Ze-Shui Liu, Pei-Pei Xie, Bo Ding, Hong-Gang Cheng, Xin Hong

Issue&Volume: 2021-03-30

Abstract: Herein we report a highly enantioselective kinetic resolution of tertiary benzyl alcohols via palladium/chiral norbornene cooperative catalysis. With simple aryl iodides as the resolution reagent, a wide range of readily available racemic tertiary benzyl alcohols are applicable to this method. Both chiral tertiary benzyl alcohols and benzo[c]chromene products are obtained in good to excellent enantioselectivities (selectivity factor up to 544). The appealing synthetic utility of the obtained enantioenriched tertiary alcohols is demonstrated by the facile preparation of several valuable chiral heterocycles. Preliminary mechanism studies include DFT calculations to explain the origin of enantiodiscrimination and control experiments to uncover the formation of a transient axial chirality during the kinetic resolution step.

DOI: 10.1002/anie.202103428

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202103428

期刊信息

Angewandte Chemie:《德国应用化学》,创刊于1887年。隶属于德国化学会,最新IF:12.959
官方网址:https://onlinelibrary.wiley.com/journal/15213773
投稿链接:https://www.editorialmanager.com/anie/default.aspx