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Axially Chiral <scp>Aryl‐Alkene‐Indole</scp> Framework: A Nascent Member of the Atropisomeric Family and Its Catalytic Asymmetric Construction

Cong‐Shuai Wang, Tian‐Zhen Li, Si‐Jia Liu, Yu‐Chen Zhang, Shuang Deng, Yinchun Jiao, Feng Shi

2020Chinese Journal of Chemistry148 citationsDOI

Abstract

Summary of main observation and conclusion 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 &gt;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.

Topics & Concepts

AlkeneChemistryEnantioselective synthesisArylIndole testAxial symmetryAxial chiralityCombinatorial chemistryChirality (physics)CatalysisStereochemistryOrganic chemistryPhysicsChiral symmetry breakingAlkylQuantum mechanicsNambu–Jona-Lasinio modelQuarkAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlgebraic structures and combinatorial models