Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives

Sheng, Feng‐Tao; Wang, Jingyi; Tan, Wei; Zhang, Yu‐Chen; Shi, Feng

doi:10.1039/d0qo01124j

Cited by 197 publications

(61 citation statements)

References 165 publications

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“…Actually, both hydrogenation and oxidation of indoles could be regarded as dearomatization of indoles [1p–s] . In 2020, Vincent[1p] and Shi [1q] reviewed the asymmetric drearomatization reactions of indoles.…”

Section: Oxidationmentioning

confidence: 99%

Recent Studies of Bifunctionalization of Simple Indoles

Wang

et al. 2021

Asian J Org Chem

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Indole structures are extremely important and widely employed in organic synthesis. This review will focus on direct bifunctionalizations of simple indoles in tandem reactions. Recent studies have been divided into four types by trigger mechanisms: (1) nucleophilic C3; (2) nucleophilic NH for cyclization; (3) reduction; (4) oxidation. Reactions with carbocations, pyridines, alkenes, alkynes, aldehydes, imines, halogenated compounds et al were discussed. We hope this review will promote future research in the use of indoles.

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Section: Oxidationmentioning

confidence: 99%

Recent Studies of Bifunctionalization of Simple Indoles

Wang

et al. 2021

Asian J Org Chem

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“…Catalytic asymmetric dearomatization (CADA) through fluorination has also been reported, but there are still few examples available [75a–c] . In 2011, Gouverneur and coworkers reported the first catalytic example [76] .…”

Section: Direct Fluorinationmentioning

confidence: 99%

Recent Developments in Enantioselective Organocatalytic Cascade Reactions for the Construction of Halogenated Ring Systems

Phillips

Pombeiro

2021

Eur J Org Chem

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Chiral halogenated substances have many applications in pharmaceuticals, agrochemicals, and materials, such as polymers, liquid crystals and as intermediates in synthesis. The presence of a halogen atom in a molecule can have a large effect in its properties; for instance, halogens are used in drugs to improve lipophilicity, membrane permeability and absorption, and even the blood‐brain barrier permeability. As highlighted in this review, there are nowadays a range of highly selective, versatile halogenating reagents, electrophilic, nucleophilic or radical in nature, which operate under mild conditions, allowing late‐stage functionalization of complex molecules in cascade reactions. Recent developments in organocatalyst design revealed novel Cinchona alkaloids derivatives, chiral phosphoric acids, amines, phosphines and several bifunctional catalysts, mostly thiourea‐ or squaramide‐based, which introduced chirality, with high levels of enantio‐ and diastereoselection, in the formation of one or multiple chiral centers in a single synthetic operation, as shown. In this review we survey the literature published in this field from 2014 to 2020.

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“…Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17][18]. Because indoles are readily available materials, the direct extension of indoles to carbazole skeletons has a great advantage [19][20][21][22][23][24][25][26][27]. Therefore, the Diels-Alder reaction of activated 2-vinylindolines or 3-vinylindolines with diverse dienophiles has become the most attractive strategy for the synthesis of carbazole deriv- atives [28][29][30][31][32][33][34][35][36][37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

Fang

Yan

Sun

et al. 2021

Beilstein J. Org. Chem.

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The p-TsOH-catalyzed Diels–Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 °C afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones or benzylideneacetone in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their acid-catalyzed Diels–Alder reaction and sequential aromatization process.

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Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives

Abstract: Chiral indole derivatives such as indolines and indolenines are important heterocyclic frameworks which constitute the core structures of many natural products and bioactive molecules. So, intensive attentions from chemists have...

Cited by 197 publications

References 165 publications

Recent Studies of Bifunctionalization of Simple Indoles

Recent Studies of Bifunctionalization of Simple Indoles

Recent Developments in Enantioselective Organocatalytic Cascade Reactions for the Construction of Halogenated Ring Systems

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

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