Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction
Efficient synthesis of optically active atropisomeric anilides through catalytic asymmetric N-arylation reaction
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DOI：
10.1021/ja042216x
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发表时间：
2005-03-23
影响因子：
15
通讯作者：
Taguchi, T
中科院分区：
文献类型：
--
作者：
Kitagawa, O;Takahashi, M;Taguchi, T
在（R）-DTBM-SEGPHOS-Pd（OAc）2催化剂存在下，4-硝基碘苯与4-叔丁基-NH-苯胺的N-芳基化反应具有较高的对映选择性（89 - 95%ee），得到了具有N-C手性轴的光学活性阻转异构体苯胺.此外，本发明的催化不对称N-芳基化的分子内形式产生具有高光学纯度（94 - 96%ee）的阻转异构内酰胺。
In the presence of (R)-DTBM-SEGPHOS-Pd(OAc)2catalyst, N-arylation ofortho-tert-butyl-NH-anilides with 4-nitroiodobenzene proceeds with high enantioselectivity (89−95% ee) to give optically active atropisomeric anilides possessing N−C chiral axis. Furthermore, the intramolecular version of the present catalytic asymmetric N-arylation gave atropisomeric lactams with high optical purity (94−96% ee).