The Application of N‐Protected 3‐Vinylindoles in Chiral Phosphoric Acid‐Catalyzed [3+2] Cyclization with 3‐Indolylmethanols: Monoactivation of the Catalyst to Vinyliminium,Advanced Synthesis & Catalysis

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The Application of N‐Protected 3‐Vinylindoles in Chiral Phosphoric Acid‐Catalyzed [3+2] Cyclization with 3‐Indolylmethanols: Monoactivation of the Catalyst to Vinyliminium
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2016-06-02 , DOI: 10.1002/adsc.201501175
Tao Fan ₁ , Hong‐Hao Zhang ₁ , Can Li ₁ , Yang Shen ₁ , Feng Shi ₁

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A highly enantioselective [3+2] cyclization of 3‐vinylindoles with isatin‐derived 3‐indolylmethanols has been established in the presence of chiral phosphoric acid, which constructed the enantioenriched cyclopenta[b]indole scaffold linking a 3‐vinylindole moiety in generally good yields, considerable diastereoselectivities and high enantioselectivities (up to 93%, >95:5 dr, >99.5:0.5 er). More importantly, this reaction utilized N‐protected 3‐vinylindoles as competent reactants, which confronted the challenge in realizing a successful monoactivation mode of chiral phosphoric acid to vinyliminium in 3‐indolylmethanol‐involved enantioselective transformations. Besides, this protocol also settled the challenge in realizing a highly enantioselective [3+2] cyclization of 3‐vinylindoles with 3‐indolylmethanols, which would serve as a useful strategy for constructing an enantioenriched cyclopenta[b]indole scaffold linking a 3‐vinylindole moiety.

中文翻译：

N保护的3-Vinylindoles在3-吲哚基甲醇催化手性磷酸催化的[3 + 2]环化中的应用：催化剂对乙烯基亚胺的单活化

在存在手性磷酸的情况下，已建立了由靛红衍生的3-吲哚基甲醇对3-乙烯基吲哚的高度对映选择性[3 + 2]环化反应，该化合物构建了对映体富集的环戊达[ b ]吲哚骨架，该骨架通常将3-乙烯基吲哚部分连接起来。收率，相当的非对映选择性和高对映选择性（高达93％，> 95：5 dr，> 99.5：0.5 er）。更重要的是，该反应利用了N-保护的3-乙烯基吲哚作为有效的反应物，这在实现由3-吲哚基甲醇参与的对映选择性转化中，成功地将手性磷酸单活化成乙烯基亚胺时面临着挑战。此外，该协议还解决了用3-吲哚基甲醇实现3-乙烯基吲哚的高度对映选择性[3 + 2]环化的挑战，这将成为构建连接3-乙烯基吲哚的对映体富集的环戊达[ b ]吲哚支架的有用策略。部分。

更新日期：2016-06-02

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