Zn-Catalyzed Enantioselective Allylation and Allenylation of Isatins by virtue of Proline-derived Chiral Ligand
Zn-Catalyzed Enantioselective Allylation and Allenylation of Isatins by virtue of Proline-derived Chiral Ligand
复制标题
脯氨酸衍生手性配体的锌催化靛红对映选择性烯丙基化和烯丙基化
DOI：
10.1039/d1cc06563g
复制
发表时间：
--
影响因子：
4.9
通讯作者：
Zhiyong Wang
中科院分区：
文献类型：
--
作者：
Kuiliang Li;Xiang Sun;Shuangshuang Zhao;Tong Li;Zhenggen Zha;Zhiyong Wang
在刘易斯酸催化下，用有机硼试剂对靛红进行了不对称烯丙基化和烯丙基化反应。该方法合成了一系列光学纯的3-烯丙基-3-羟基羟吲哚和3-丙二烯基-3-羟基羟吲哚，产率高达99%，对映选择性高达97% ee。通过密度泛函理论计算支持了可能的过渡态，并提出了相应的反应机理。建立了一个克规模的实验和进一步的功能化，这些手性3-羟基羟吲哚。
An asymmetric allylation and allenylation of isatins with facile organoboron reagents was developed under the catalysis of a Lewis acid. A series of optically pure 3-allyl-3-hydroxyoxindoles and 3-allenyl-3-hydroxyoxindoles can be obtained in excellent yields (up to 99% yield) and high enantioselectivities (up to 97% ee). The possible transition state was supported by DFT calculation and the corresponding mechanism was proposed. A gram scale experiment and further functionalization of these chiral 3-hydroxyoxindoles are established.