Stereoselective Synthesis of Indolyl-<i>C</i>-glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2-Alkynylanilines with Glycals

Xiao, Xiao; Han, Puren; Wan, Jie-Ping; Liu, Jianchao

doi:10.1021/acs.orglett.3c02688

Cited by 8 publications

(2 citation statements)

References 50 publications

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“…In addition, the conversions of the exemplary product were inspected to establish the promising synthetic utilization of this method. Recently, Liu research group [52] explored cascade cyclization via aminopalladation followed by Heck glycosylation for the synthesis of indolyl-C-glycosides (Scheme 12). The reaction occurred via an intramolecular aminopalladation of alkyne resulted with 3indolyl-Pd species and followed by addition to glycals via Heck insertion.…”

Section: Heterocyclization and C-glycosylation Sequencementioning

confidence: 99%

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Sangwan,

Azeem,

Kumar Mandal

2024

Adv Synth Catal

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Recently, C‐glycosidic bonds have emerged as pivotal elementary units present in many naturally occurring alkaloids as well as in pharmaceutically active molecules. Because of the stability and great utility of C‐glycosides, synthetic approaches en route to the C‐C bond formation have gradually become a center of attraction in carbohydrate chemistry. Towards these researches, C‐glycosylation with heteroaryl moieties like indole, and tryptophan can remarkably expand the functional and structural evolution, which has great value for medicinal chemists and chemical biologists. The indolyl and tryptophan‐C‐glycosides have unique structures and biological activities that have attracted a number of synthetic studies. Therefore, these motifs have possessed an extensive interest in the direction of efficient synthesis. Herein, this review systematically summarizes the classical approaches to C‐heteroaryl glycosides mainly focusing on indole and tryptophan synthesis. Furthermore, highlighted the recently developed metal‐catalyzed C‐H functionalization and photoinduced cross‐coupling strategies that aim to control the regioselectivity and diastereoselectivity of the reaction in carbohydrate chemistry. In view of reaction type, mechanism, and status, this review will cover the synthesis of indole and tryptophan C‐heteroaryl glycosides with diverse regio‐ and diastereoselectivity from four perspectives which include a) conventional approach, b) heterocyclization and C‐glycosylation sequence, c) metal‐catalyzed C‐H functionalization, and d) photoinduced cross‐coupling. 1. Introduction 2. Strategies for the synthesis of indolyl and tryptophan‐C‐glycosides 2.1. Conventional approach 2.2. Heterocyclization and C‐glycosylation sequence 2.3. Metal‐catalyzed C‐H functionalization 2.4. Photoinduced cross‐coupling 3. Summary and Outlook

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Section: Heterocyclization and C-glycosylation Sequencementioning

confidence: 99%

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Sangwan,

Azeem,

Kumar Mandal

2024

Adv Synth Catal

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“…As shown in Scheme e, 1,6-enyne 1 was envisioned as the starting point of the reaction sequence. Amino-palladation cyclization of 1,6-enyne 1 should form indole intermediate I . Migratory insertion of the appended alkene to the indol-3-yl palladium complex generates intermediate II with a quaternary stereocenter .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral Polycyclic Indoles via Pd(II)-Catalyzed Sequential Cyclization and Carbonylation

Chen,

Zhou,

Xue

et al. 2024

ACS Catal.

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Asymmetric tandem Heck and carbonylation reactions provide an efficient route to synthesize biologically important chiral cyclic compounds with a carbonyl group and have attracted increasing research interests. However, this type of reaction relies on the initiation from the oxidative addition of aryl halides or pseudo halides, resulting in a low atomic economy of the reaction. In addition, this protocol has not adequately demonstrated the reactivity and generality of heteroarene halides. Meanwhile, the asymmetric Wacker-type cyclization and carbonylation reactions are plagued by narrow substrate scope and low enantioselectivity and remain underexplored. Herein, we describe a Pd(II)-catalyzed asymmetric sequential cyclization and carbonylation reaction of 1,6-enynes and analogues with carbon monoxide (CO). This catalytic system tolerates a broad scope of nucleophiles, including phenols, alcohols, and amines. This reaction sequence forms four chemical bonds, two rings, and up to three stereocenters in a single step. This strategy allows for the convenient access to a variety of polycyclic compounds in good yields with good enantio- and diastereoselectivities, including indoles, benzofurans, indole- or benzofuran-fused bicyclo[3.2.1]octanes, and indole-fused bicyclo[4.2.1]nonane.

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Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art

Antonini,

Petrosilli,

Giussani

et al. 2024

Eur J Org Chem

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The intricate nature of carbohydrate structures has prompted the scientific community to seek efficient protocols for their manipulation. Lengthy synthetic pathways, often necessary to achieve complex sugar structures, pose challenges not only in terms of time and cost but also regarding environmental sustainability. Consequently, domino transformations serve as valuable tools in streamlining drug discovery processes. Sequential procedures involving fewer steps and minimal isolation/purification steps are particularly appealing to organic chemists in the field of carbohydrate chemistry. This review highlights several examples of domino transformations applied to carbohydrates, aiming to summarize their chemical potential in delivering sugar‐based compounds with significant applications in the generation of new chemical scaffolds for drug discovery and chemical biology.

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Stereoselective Synthesis of Indolyl-C-glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2-Alkynylanilines with Glycals

Cited by 8 publications

References 50 publications

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Recent Advances and Strategies towards Synthesis of Indolyl and Tryptophan‐C‐Glycoside Scaffolds

Synthesis of Chiral Polycyclic Indoles via Pd(II)-Catalyzed Sequential Cyclization and Carbonylation

Unleashing the Power of Domino Reactions on Carbohydrates: State of the Art

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