Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles

Rassu Gloria; Curti Claudio; Zambrano Vincenzo; Pinna Luigi; Brindani Nicoletta; Pelosi Giorgio; Zanardi Franca

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Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles

机译：利用吲哚基亚甲基丙二腈的远端反应性：不对称的有机化合物催化的[4 + 2]环加成反应与Enals能够实现难以捉摸的二氢咔唑的组装

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An unprecedented technique for the in situ generation of indolyl ortho-quinodimethanes from 2-methylindole-based methylenemalononitriles by amine-mediated remote C(sp(3))-H deprotonation was developed. These intermediates were efficiently trapped by diverse enals to provide a rapid entry to 2,9-dihydro-1H-carbazole-3-carboxyaldehyde structures through a formal asymmetric [4+2] eliminative cycloaddition governed by alpha,alpha,-adiphenylprolinol trimethylsilyl ether catalyst.

机译：开发了一种空前的技术，通过胺介导的远程C（sp（3））-H脱质子化从2-甲基吲哚基的亚甲基丙二腈原位生成吲哚基邻喹啉甲烷。这些中间体被各种烯类有效地捕获，从而通过由α，α，-二苯基脯氨醇三甲基甲硅烷基醚催化剂控制的形式不对称[4 + 2]消除环加成反应，快速进入2,9-二氢-1H-咔唑-3-羧醛结构。

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《Chemistry: A European journal》 |2016年第36期|共4页
作者
Rassu Gloria; Curti Claudio; Zambrano Vincenzo; Pinna Luigi; Brindani Nicoletta; Pelosi Giorgio; Zanardi Franca;
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正文语种 eng
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asymmetric synthesis; cycloaddition; heterocycles; organocatalysis; vinylogy;

机译：不对称合成环加成杂环有机催化葡萄学;

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1. Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles [J] . Rassu Gloria, Curti Claudio, Zambrano Vincenzo, Chemistry: A European journal . 2016,第36期

机译：利用吲哚基亚甲基丙二腈的远端反应性：不对称的有机化合物催化的[4 + 2]环加成反应与Enals能够实现难以捉摸的二氢咔唑的组装
2. Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles [J] . Rassu Gloria, Curti Claudio, Zambrano Vincenzo, Chemistry: A European journal . 2016,第36期

机译：利用吲哚基亚甲基丙二腈的远端反应性：不对称的有机化合物催化的[4 + 2]环加成反应与Enals能够实现难以捉摸的二氢咔唑的组装
3. Exploiting the Distal Reactivity of Indolylmethylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles [J] . Curti Claudio, Rassu Gloria, Brindani Nicoletta, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2016,第23期

机译：利用吲哚基亚甲基丙二腈的远端反应性：不对称的有机化合物[4 + 2]环加成与Enals可以实现难以捉摸的二氢咔唑的组装
4. Synergetic iridium and amine catalysis enables asymmetric 4+2 cycloadditions of vinyl aminoalcohols with carbonyls [O] . Mao-Mao Zhang, Ya-Ni Wang, Bao-Cheng Wang, -1

机译：铱和胺的协同催化作用可实现乙烯基氨基醇与羰基的不对称4 + 2环加成
5. Synergetic iridium and amine catalysis enables asymmetric 4+2 cycloadditions of vinyl aminoalcohols with carbonyls [O] . Mao-Mao Zhang, Ya-Ni Wang, Bao-Cheng Wang, 2019

机译：协同铱和胺催化使得不对称4 + 2环加成乙烯基氨基醇与羰基醇

Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles

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