Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

Hattori, Tetsutaro; Iwato, Hiroaki; Natori, Koichi; Miyano, Sotaro

doi:10.1016/j.tetasy.2004.01.021

Cited by 8 publications

(1 citation statement)

References 49 publications

(3 reference statements)

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“…These are also useful starting materials for the synthesis of axially chiral biarylamide- and biarylamine-derived ligands and axially chiral ammonium betaine organocatalysts . Therefore, their asymmetric synthesis has been well investigated to date, and several successful examples have been reported. − As a cross-coupling approach, the diastereoselective nucleophilic aromatic substitution on chiral 1-alkoxy-2-naphtholates with aryl Grignard reagents ,, and the enantioselective Suzuki−Miyaura cross-coupling were reported (Scheme ). As a conceptually different approach, a number of enantioselective ring-opening reactions of biaryl lactones, possessing configurationally unstable biaryl axes, were reported (Scheme ) …”

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Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition

Ogaki

Shibata

Noguchi³

et al. 2011

J. Org. Chem.

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Axially chiral hydroxy carboxylic acid derivatives were successfully synthesized with high yields and ee values by the cationic rhodium(I)/axially chiral biaryl bisphosphine complex-catalyzed enantioselective [2 + 2 + 2] cycloaddition. Axially chiral hydroxy and dihydroxy carboxylic acid derivatives, bearing the aryl group at the ortho-position of the alkoxycarbonyl group, were also synthesized with high regio- and enantioselectivity.

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confidence: 99%

Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition

Ogaki

Shibata

Noguchi³

et al. 2011

J. Org. Chem.

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Indium‐Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2‐Methyl‐3‐(thien‐2‐yl)‐1 H ‐indole

Nagase

Tsuchimoto

2014

Organic Syntheses

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The article describes the synthesis of 2‐methyl‐3‐(thien‐2‐yl)‐1 H ‐indole on a 0.25 mmol scale carried out with 2‐methyl‐1H‐indole and 2‐methoxythiophene in a 1.3:1 molar ratio. The desired product is isolated as a pure form by column chromatography on silica gel. In order to obtain the pure product in such a large‐scale synthesis, the use of a slight excess molar amount of not 2‐methyl‐1H‐indole but 2‐methoxythiophene is important.

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Indium‐Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution

et al. 2010

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Asymmetric synthesis of ternaphthalenes via an ester-mediated nucleophilic aromatic substitution reaction

Cited by 8 publications

References 49 publications

Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition

Enantioselective Synthesis of Axially Chiral Hydroxy Carboxylic Acid Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition

Indium‐Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution: Preparation of 2‐Methyl‐3‐(thien‐2‐yl)‐1 H ‐indole

Indium‐Catalyzed Heteroaryl–Heteroaryl Bond Formation through Nucleophilic Aromatic Substitution

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