Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles
Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles
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DOI：
10.1002/adsc.200700151
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发表时间：
2007-08-01
影响因子：
5.4
通讯作者：
Uraguchi, Daisuke
中科院分区：
文献类型：
--
作者：
Terada, Masahiro;Yokoyama, Shigeko;Uraguchi, Daisuke
在BINOL衍生的单磷酸催化下，N-叔丁基二甲基硅基吲哚与N-叔丁氧羰基芳香亚胺的1，2-氮杂-Friedel-Crafts反应具有高度的对映选择性.本方法提供了有效的途径，3-吲哚基甲烷胺与芳基取代基在优异的对映体选择性（高达98%ee）。发现在联萘骨架3，3 ′-位引入不同取代基的单磷酸催化剂之间存在对映体选择性反转。我们还计算了单磷酸催化剂的三维结构，以推测立体化学结果的反转。
A highly enantioselective 1,2-aza-Friedel-Crafts reaction of N-tert-butyldimethylsilylindole with N-tert-butoxycarbonyl aromatic imines is demonstrated using a BINOL-derived monophosphoric acid catalyst. The present approach provides efficient access to 3-indolylmethaneamines with aryl substituents in excellent enantioselectivities (up to 98 % ee). An inversion in the sense of enantioselection was found between monophosphoric acid catalysts bearing different substituents introduced at the 3,3'-position of binaphthyl backbone. We also calculated the three-dimensional structure of the monophosphoric acid catalysts to speculate on the inversion of the stereochemical outcome.