Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds.
Stereoselective synthesis of both enantiomers of N-aryl indoles with axially chiral N-C bonds.
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DOI：
10.1002/chin.200736101
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发表时间：
2007-03
期刊：
影响因子：
--
通讯作者：
K. Kamikawa;Shunsuke Kinoshita;M. Furusyo;S. Takemoto;H. Matsuzaka;M. Uemura
中科院分区：
文献类型：
--
作者：
K. Kamikawa;Shunsuke Kinoshita;M. Furusyo;S. Takemoto;H. Matsuzaka;M. Uemura
通过平面手性tricarbonyl(2，6-disubstituted-1-fluorobenzene)chromium络合物的立体选择性芳香取代反应，合成了具有轴向手性N-C键的N-芳基吲哚。产物的立体化学高度依赖于取代基在吲哚中的位置。当使用在2-位没有取代基的吲哚时，非对映选择性地得到了与三羰基铬片段相反取向的N-芳基吲哚铬配合物。相反，2-取代吲哚得到的N-芳基吲哚在三羰基铬碎片和吲哚的苯环之间具有同步取向。这些结果表明，我们利用一个相同的平面手性芳香铬络合物成功地合成了N-芳基吲哚的两个对映体。
N-Aryl indoles with axially chiral N-C bonds were synthesized by stereoselective nucleophilic aromatic substitution reactions of planar chiral tricarbonyl(2,6-disubstituted-1-fluorobenzene)chromium complexes. The stereochemistry of the products is highly dependent on the position of the substituent in the indole. When indoles devoid of a substituent at the 2-position were used, N-aryl indole chromium complexes having anti orientation with respect to the tricarbonylchromium fragment were obtained diastereoselectively. In contrast, 2-substituted indoles gave the N-aryl indoles with syn orientation between the tricarbonylchromium fragment and the benzene ring of the indole. These results demonstrate that we have succeeded in synthesizing both enantiomers of N-aryl indoles utilizing an identical planar chiral arene chromium complex.