Gold-catalyzed enantioselective functionalization of indoles

Milcendeau, Pierre; Sabat, Nazarii; Ferry, Angélique; Guinchard, Xavier

doi:10.1039/d0ob01245a

Cited by 51 publications

(14 citation statements)

References 92 publications

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“…Homogeneous gold catalysis has also been utilized in the field of indole functionalization. , Indoles represent one of the most intensively studied heterocyclic systems in diverse areas of research especially in pharmaceutical, agrochemical, and material sciences. Formation of indole-tethered five- and six-membered rings via Au-catalyzed transformations was likewise reported in the literature including preparation of carbazoles and its derivatives. − …”

Section: Introductionmentioning

confidence: 99%

Construction of Medium-Sized Rings by Gold Catalysis

2020

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Compounds having cyclic molecular frameworks are highly regarded for their abundance and diverse utilities. In particular, medium-sized carbocycles and heterocycles exist in a broad spectrum of natural products, bioactive therapeutics, and medicinally significant synthetic molecules. Metal-mediated methods have been developed for the preparation of compounds containing a medium-sized ring (MSR) through cyclization of different classes of substrates and acyclic precursors. This review focuses on the methodologies for construction of MSRs via gold catalysis. Given the challenges in enabling the assembly of different ring sizes, we present here accounts on Au-mediated cyclization giving notable 7-membered and medium-sized (8–11-membered ring) structures. Emphasis on the pathway and mode of cyclization and the selection of precursors ranging from structurally biased compounds were outlined. Reactivity patterns and the choice of efficient Au catalysts for controlling reaction performance and selectivity in addition to mechanistic attributes are examined.

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Section: Introductionmentioning

confidence: 99%

Construction of Medium-Sized Rings by Gold Catalysis

2020

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“…Additionally, the corresponding carbazole derivatives also show important applications in various functional materials [4][5][6][7]. Owing to their remarkable significance, developing convenient synthetic protocols for functionalized tetrahydrocarbazoles has attracted continual attention in synthetic and pharmaceutical chemistry [8][9][10][11][12][13][14][15]. Among many well-designed strategies for the synthesis of tetrahydrocarbazoles, the direct assembly of the tetrahydrocyclohexenyl ring with readily available functionalized indoles as pre-cursors has proven to be one of the most efficient synthetic protocols [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

Zhan¹,

Fang²,

Sun³

et al. 2022

Beilstein J. Org. Chem.

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In the presence of copper sulfate, three- or four-component reactions of 2-methylindole, aromatic aldehydes and various cyclic dienophiles in refluxing toluene afforded diverse spirotetrahydrocarbazoles. This reaction is an important development of the Levy reaction by using 2-methylindole to replace ethyl indole-2-acetate and successfully provides facile access to important polysubstituted spiro[carbazole-3,3'-indolines], spiro[carbazole-2,3'-indolines], spiro[carbazole-3,5'-pyrimidines] and spiro[carbazole-3,1'-cycloalkanes] in satisfactory yields and with high diastereoselectivity.

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“…Sandtorv [1c] and Djakovitch [1d] respectively summarized the transition metal‐catalyzed C‐H [1c,d] or N‐H [1d] activation of indoles. During these years, Guinchard, [1e] Jia, [1f] Petrini [1g] and Bandini [1h] all collected the enantioselective indole transformations. Recently, both Gaich [1i] and Eycken [1j] depicted the light‐mediated chemistry of indoles, while the Ye [1k] reviewed the electrochemical functionalization of indoles.…”

Section: Introductionmentioning

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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Gold-catalyzed enantioselective functionalization of indoles

Abstract: This review documents the potential of enantioselective gold catalysis for the functionalization of indoles.

Cited by 51 publications

References 92 publications

Construction of Medium-Sized Rings by Gold Catalysis

Construction of Medium-Sized Rings by Gold Catalysis

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

Recent Studies of Bifunctionalization of Simple Indoles

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