Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′-Bisindole Skeletons
Design and Catalytic Asymmetric Construction of Axially Chiral 3,3′-Bisindole Skeletons
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DOI：
10.1002/anie.201811177
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发表时间：
2019-03-04
影响因子：
16.6
通讯作者：
Shi, Feng
中科院分区：
文献类型：
--
作者：
Ma, Chun;Jiang, Fei;Shi, Feng
通过2-取代3,3 '-双吲哚与3-吲哚甲醇的有机催化不对称加成反应，首次建立了具有轴向和中心手性的3,3 '-双吲哚骨架的催化不对称结构（产率高达98%，所有>95:5 d.r, > 99% ee）。该反应也代表了第一个高度对映选择性的轴手性3,3 '-双吲哚骨架结构，并利用了在前手性3,3 '-双吲哚的邻位上引入一个大基团的策略。该反应不仅为在一次操作中同时控制轴手性和中心手性提供了很好的例子，而且为从前手性底物催化对映选择性构建轴手性3,3 '-双吲哚骨架提供了新的策略。
The first catalytic asymmetric construction of 3,3 '-bisindole skeletons bearing both axial and central chirality has been established by organocatalytic asymmetric addition reactions of 2-substituted 3,3 '-bisindoles with 3-indolylmethanols (up to 98 % yield, all >95:5 d.r., >99 % ee). This reaction also represents the first highly enantioselective construction of axially chiral 3,3 '-bisindole skeletons, and utilizes the strategy of introducing a bulky group to the ortho-position of prochiral 3,3 '-bisindoles. This reaction not only provides a good example for simultaneously controlling axial and central chirality in one operation, but also serves as a new strategy for catalytic enantioselective construction of axially chiral 3,3 '-bisindole backbones from prochiral substrates.