Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines

Zhang, Zhixin; Wang, Xuan; Jiang, Jia-Tian; Chen, Jie; Zhu, Xin‐Qi; Ye, Long‐Wu

doi:10.1016/j.cclet.2022.06.070

Cited by 23 publications

(6 citation statements)

References 112 publications

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“…Chiral indoline structure is a key structural motif in numerous natural alkaloids and bioactive relevant molecules. [8] Therefore, the direct catalytic asymmetric dearomatization of indoles based on their electron-rich property has resulted in significant achievements in the past decades. [2d,e] Complementarily, since the pioneering work of Gribble and Mancini (Scheme 2), the catalytic asymmetric nucleophilic dearomative cycloaddition reaction of 3-nitroindoles has been recognised as an alternative powerful protocol for the facile construction of chiral indoline structures.…”

Section: Asymmetric Dearomative Annulations Of 3-nitroindolesmentioning

confidence: 99%

Recent Progress of Electron‐Withdrawing‐Group‐Tethered Arenes Involved Asymmetric Nucleophilic Aromatic Functionalizations

Wang

2022

Adv Synth Catal

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Electron-withdrawing groups (EWG) have emerged as a powerful tool for the activation of various arenes to promote nucleophilic dearomative additions for the construction of complicated chiral cyclic structures under asymmetric catalytic systems. Nitro-indoles, nitro-benzofurans/benzothiophenes, and related nitro-heteroarenes are widely applied in the reaction with various nucleophiles to construct various enantioenriched polycyclic skeletons via the asymmetric dearomatization process. Meanwhile, the electron-deficient azo-group and nitroso-group are an alternative powerful tool for the activation of arenes, which enable formal nucleophilic aromatic arylations with various electrophilic aromatics to construct novel chiral biaryl atropisomers. Besides, azo-naphthanenes are served as dipolar surrogates in the reaction with nucleophilic dipolarophiles to proceed asymmetric cycloadditions to construct chiral polycyclic skeletons. The EWG-tethered arene has proven to be a versatile protocol for the construction of structurally diversified chiral backbones. This review summarizes the latest progress of the EWG-tethered arenes involved asymmetric transformations under organo-or transition metal catalysis.1.

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Section: Asymmetric Dearomative Annulations Of 3-nitroindolesmentioning

confidence: 99%

Recent Progress of Electron‐Withdrawing‐Group‐Tethered Arenes Involved Asymmetric Nucleophilic Aromatic Functionalizations

Wang

2022

Adv Synth Catal

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“…In line with our continuing interest in the catalytic asymmetric dearomatization (CADA) reactions, we have developed a series of chiral phosphoric acid (CPA) catalyzed dearomative cyclization reactions of indoles/pyrroles bearing a pendant nucleophile with external electrophiles . In 2012, Zhang and Antilla reported an elegant asymmetric aminative dearomatization of tryptamine derivatives .…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Dearomatization of Indoles with Azodicarboxylates via Cascade Electrophilic Amination/Aza-Prins Cyclization/Phenonium-like Rearrangement

et al. 2023

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Herein, we report a highly efficient synthesis of enantioenriched aza-[3.3.1]-bicyclic enamines and ketones, a class of structural cores in many natural products, via asymmetric dearomatization of indoles with azodicarboxylates. The reaction is initiated by electrophilic amination and followed by aza-Prins cyclization/phenonium-like rearrangement. A newly developed fluorine-containing chiral phosphoric acid displays excellent activity in promoting this cascade reaction. The absence or presence of water as the additive directs the reaction pathway toward either enamine or ketone products in high yields (up to 93%) with high enantiopurity (up to 98% ee). Comprehensive density functional theory (DFT) calculations reveal the energy profile of the reaction and the origins of enantioselectivity and water-induced chemoselectivity.

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“…2,3 Among them, the catalytic asymmetric dearomatization (CADA) of substituted indoles has been proved to be a powerful route for the synthesis of three-dimensional polycyclic indolines. 3,4 In particular, transition metal-catalyzed reductive Heck reactions or a Heck/benzyl-metal capture sequence represents a conspicuous strategy for dearomative functionalization of indole derivatives. 3 f – h Along this line, great progress has been made in palladium-catalyzed racemic dearomative difunctionalization of substituted indoles with diverse trapping reagents.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis

Huang,

Tan,

Zhang

et al. 2023

Org. Chem. Front.

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Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines

Cited by 23 publications

References 112 publications

Recent Progress of Electron‐Withdrawing‐Group‐Tethered Arenes Involved Asymmetric Nucleophilic Aromatic Functionalizations

Recent Progress of Electron‐Withdrawing‐Group‐Tethered Arenes Involved Asymmetric Nucleophilic Aromatic Functionalizations

Asymmetric Dearomatization of Indoles with Azodicarboxylates via Cascade Electrophilic Amination/Aza-Prins Cyclization/Phenonium-like Rearrangement

Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis

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