Axially Chiral Aryl‐Alkene‐Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction,Chinese Journal of Chemistry

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Axially Chiral Aryl‐Alkene‐Indole Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2020-04-04 , DOI: 10.1002/cjoc.202000131
Cong‐Shuai Wang ₁ , Tian‐Zhen Li ₁ , Si‐Jia Liu ₁ , Yu‐Chen Zhang ₁ , Shuang Deng ₂ , Yinchun Jiao ₂ , Feng Shi ₁

Affiliation

A new class of axially chiral aryl‐alkene‐indole frameworks have been designed, and the first catalytic asymmetric construction of such scaffolds has been established by the strategy of organocatalytic (Z/E)‐selective and enantioselective (4+3) cyclization of 3‐alkynyl‐2‐indolylmethanols with 2‐naphthols or phenols (all >95 : 5 E/Z, up to 98% yield, 97% ee). This reaction also represents the first catalytic asymmetric construction of axially chiral alkene‐heteroaryl scaffolds, which will add a new member to the atropisomeric family. This approach has not only confronted the great challenges in constructing axially chiral alkene‐heteroaryl scaffolds but also provided a powerful strategy for the enantioselective construction of axially chiral aryl‐alkene‐indole frameworks.

中文翻译：

轴向手性芳基-烯烃-吲哚骨架：阻转异构家族的新生成员及其催化不对称结构

设计了一类新的轴向手性芳基-烯烃-吲哚骨架，并通过3的有机催化（Z / E）选择性和对映选择性（4 + 3）环化策略建立了此类支架的第一个催化不对称结构。带有2-萘酚或苯酚的炔基-2-吲哚基甲醇（均> 95：5 E / Z，产率高达98％，ee高达97％）。该反应也代表了轴向手性烯烃-杂芳基骨架的第一个催化不对称结构，它将为阻转异构体家族增加一个新成员。这种方法不仅在构建轴向手性烯烃-杂芳基骨架方面面临巨大挑战，而且为轴向手性芳基烯烃-吲哚骨架的对映选择性构建提供了强有力的策略。

更新日期：2020-04-04

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