A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles

Sun, Yin-Wei; Tang, Xiang‐Ying; Shi, Min

doi:10.1039/c5cc05808b

Cited by 21 publications

(5 citation statements)

References 64 publications

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“…The challenging synthesis of medium-sized heterocycles possessing a trans double bond was described by Tang, Shi, and co-workers ( Scheme 36 ) [ 81 ]. They described a gold(I)-catalyzed 1,2-acyloxy migration–intramolecular cyclopropanation–ring enlargement cascade reaction.…”

Section: Methods Using Gold- or Silver-catalyzed Reactionsmentioning

confidence: 99%

“…The reaction proceeded through an activation of alkyne by cationic gold, which promoted a 5-endo-dig hydroamination followed by 8-endo-dig hydroarylation. The challenging synthesis of medium-sized heterocycles possessing a trans double bond was described by Tang, Shi, and co-workers (Scheme 36) [81]. They described a gold(I)-catalyzed 1,2acyloxy migration-intramolecular cyclopropanation-ring enlargement cascade reaction.…”

Section: Carbon-carbon Bond Formationmentioning

confidence: 99%

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Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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Medium-sized heterocycles (with 8 to 11 atoms) constitute important structural components of several biologically active natural compounds and represent promising scaffolds in medicinal chemistry. However, they are under-represented in the screening of chemical libraries as a consequence of being difficult to access. In particular, methods involving intramolecular bond formation are challenging due to unfavorable enthalpic and entropic factors, such as transannular interactions and conformational constraints. The present review focuses on the synthesis of medium-sized heterocycles by transition-metal-catalyzed intramolecular cyclization, which despite its drawbacks remains a straightforward and attractive synthesis strategy. The obtained heterocycles differ in their nature, number of heteroatoms, and ring size. The methods are classified according to the metal used (palladium, copper, gold, silver), then subdivided according to the type of bond formed, namely carbon–carbon or carbon–heteroatom.

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Section: Methods Using Gold- or Silver-catalyzed Reactionsmentioning

confidence: 99%

Section: Carbon-carbon Bond Formationmentioning

confidence: 99%

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

et al. 2020

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“…Tang and Shi's group explored ten‐ or eleven‐membered heterocycle synthetic pathway (Scheme 52). [95] The gold(I)‐catalyzed synthetic protocol followed the sequential steps of 1,2‐acyloxy migration, intermolecular cyclopropanation, and ring enlargement cascade reaction. The intermolecular reaction of furan derivative at C‐5 position 131 was obtained in presence of 2.5 mol% Me 4 t BuXPhosAu(MeCN)OTf in 1,2‐dichloroethane at room temperature to get the desired product 132 in moderate to excellent yield (56–96 %).…”

Section: Double Cascade Reactionsmentioning

confidence: 99%

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Ghosh

Bhakta

2022

The Chemical Record

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This review summarizes recent developments (from 2006 to 2022) in numerous important and efficient carbo-and heterocycle generations using gold-catalyzed cascade protocols. Herein, methodologies involve selectivity, cost-effectiveness, and ease of product formation being controlled by the ligand as well as the counter anion, catalyst, substrate, and reaction conditions. Gold-catalyzed cascade reactions covered different strategies through the compilation of various approaches such as cyclization, hydroarylation, intermolecular and intramolecular cascade reactions, etc. This entitled reaction is also useful for the synthesis of spiro, fused, bridged carbo-and heterocycles.

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“…The first group of methods is based on the use of 3-substituted furans. For example, the intramolecular Friedel–Crafts alkylation reaction ( Scheme 1a ) of alcohols [ 9 – 11 ], alkenes [ 12 ] or acetylenes [ 13 ] affords the desired tetrahydrofuro[3,2- c ]pyridines. A related method is based on a Au(I)-catalyzed domino sequence dearomatization/ ipso -cyclization/Michael-type Friedel–Crafts alkylation ( Scheme 1b ) [ 14 – 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

Mendogralo,

Uchuskin

2023

Beilstein J. Org. Chem.

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A semi-one-pot method for the synthesis of 4-substituted tetrahydrofuro[3,2-c]pyridines by the Pictet–Spengler reaction was developed. The method is based on the condensation of easily accessibly 2-(5-methylfuran-2-yl)ethanamine with commercially available aromatic aldehydes followed by acid-catalyzed Pictet–Spengler cyclization. Using this approach, we synthesized a range of 4-substituted tetrahydrofuro[3,2-c]pyridines in reasonable yields. The reactivity of some of the products was investigated and selected synthetic transformations of the obtained tetrahydrofuro[3,2-c]pyridines were shown.

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A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: syntheses of medium-sized heterocycles

Cited by 21 publications

References 64 publications

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Synthesis of Medium-Sized Heterocycles by Transition-Metal-Catalyzed Intramolecular Cyclization

Advancements in Gold‐Catalyzed Cascade Reactions to Access Carbocycles and Heterocycles: An Overview

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

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