The Synthesis of η2-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles
The Synthesis of η2-β-Vinylpyrrole Complexes and Their Conversion to Highly Substituted Indoles
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DOI：
10.1021/ja961072m
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发表时间：
1996-07
影响因子：
15
通讯作者：
L. M. Hodges;M. L. Spera;and Marcus W. Moody;W. Harman
中科院分区：
文献类型：
--
作者：
L. M. Hodges;M. L. Spera;and Marcus W. Moody;W. Harman
以1-甲基吡咯配合物为原料，在吡咯环的β碳C（3）上进行亲电加成反应，合成了一系列4，5-η2-Os（II）五胺-3-乙烯基吡咯配合物。本文介绍了四种合成β-乙烯基吡咯配合物的独立路线，每种路线在侧双键上引入不同的官能团。这些配合物的未配位部分在化学和结构上类似于氨基二烯，因此容易与适当活化的亲二烯体发生狄尔斯-桤木反应，生成5，6，7，7 a-四氢吲哚核。这些四氢吲哚配合物可以被DDQ解络合和氧化，生成一系列高度官能化的吲哚。
A series of 4,5-η2-Os(II)pentaammine-3-vinylpyrrole complexes are synthesized from the corresponding 1-methylpyrrole complex by an electrophilic addition at the β-carbon, C(3), of the pyrrole ring. Four independent synthetic routes to β-vinylpyrrole complexes are described, each introducing different functionality on the pendant double bond. The uncoordinated portion of these complexes chemically and structurally resembles an aminodiene and as such readily undergoes Diels−Alder reactions with suitably activated dienophiles to generate the 5,6,7,7a-tetrahydroindole nucleus. These tetrahydroindole complexes can be decomplexed and oxidized with DDQ to generate a series of highly functionalized indoles.