New organolithium addition methodology to diversely functionalized indoles
New organolithium addition methodology to diversely functionalized indoles
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DOI：
10.1021/ja034283h
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发表时间：
2003-04-09
影响因子：
15
通讯作者：
O'Shea, DF
中科院分区：
文献类型：
--
作者：
Coleman, CM;O'Shea, DF
介绍了一种合成二取代吲哚的新方法。Boc-保护的邻氨基苯乙烯进行烷基锂加成反应，从而产生锂化中间体，其在与特定亲电试剂反应时在反应的亲电试剂和邻氨基取代基之间建立级联反应过程，促进原位闭环，随后脱水，以产生吲哚环系统。该方法通过合成一系列3，5-、1，3，5-和2，3，5-取代的吲哚来证明。
A novel synthetic approach to diversely functionalized indoles is described. Boc-protectedortho-aminostyrenes undergo an alkyllithium addition reaction, thereby generating a lithiated intermediate, which upon reaction with specific electrophiles sets up a cascade reaction process between the reacted electrophile andortho-amino substituent, facilitating an in situ ring closure, followed by dehydration, to generate an indole ring system. This methodology is demonstrated by the synthesis of a range of 3,5-, 1,3,5-, and 2,3,5-substituted indoles.