Stereoselective formation of carbon-carbon bonds via SN2-displacement:: Synthesis of substituted cycloalkyl[b]indoles
Stereoselective formation of carbon-carbon bonds via SN2-displacement:: Synthesis of substituted cycloalkyl[b]indoles
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DOI：
10.1021/jo051146p
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发表时间：
2005-10-14
影响因子：
3.6
通讯作者：
Tillyer, RD
中科院分区：
文献类型：
--
作者：
Hillier, MC;Marcoux, JF;Tillyer, RD
完成了取代环烷基[b]吲哚的不对称合成。该方法的主要特点是(1)利用JAPP-Klingemann缩合/Fischer环合反应制备环烷基吲哚；(2)这些杂环酮与(S)-OAB进行不对称的硼烷还原得到对映体纯醇；(3)在Mitsunobu条件下，这些吲哚醇底物与碳亲核体进行立体选择性的S(N)2-置换，从而形成C-1或C-3叔碳立体中心。三甲基膦(PMe3)和双(2，2，2-三氯乙基)偶氮二甲酸酯(TCEAD)的使用对Mitsunobu的脱水烷基化反应有影响。
A general asymmetric synthesis of substituted cycloalkyl[b]indoles has been accomplished. The key features of this approach are (1) the utilization of a Japp-Klingemann condensation/Fischer cyclization to prepare cycloalkyl[b]indolones, (2) the asymmetric borane reduction of these heterocyclic ketones with (S)-OAB to obtain enantiomerically pure alcohols, and (3) the stereoselective S(N)2-displacement of these indole alcohol substrates with a carbon nucleophile under Mitsunobu conditions to set the C-1 or C-3 tertiary carbon stereocenter. The use of trimethylphosphine (PMe3) and bis(2,2,2-trichloroethyl) azodicarboxylate (TCEAD) was found to have an effect on the Mitsunobu dehydrative alkylation.