Divergent pathways for reactions of CF3-containing Isobenzofuran-1-ones and amines

Mitobe, Kana; Kawasaki‐Takasuka, Tomoko; Agou, Tomohiro; Kubota, Toshio; Yamazaki, Takashi

doi:10.1016/j.jfluchem.2018.11.012

Cited by 6 publications

(3 citation statements)

References 25 publications

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“…The formation of the new stereocenter bearing the trifluoromethyl group would imply the highly diastereoselective addition of the aza-nucleophile on the epimerized trifluoromethyl ketone. The aza-nucleophile could be the benzyl amine (intermolecular reaction) or the benzyl amide resulting from the transamidation of the Weinreb amide (intramolecular reaction) . According to the stereochemical outcome of the reaction, regardless of the nucleophile, the addition to the trifluoromethyl ketone would happen via the Felkin-Anh transition state TS-2 , , as shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

“…The aza-nucleophile could be the benzyl amine (intermolecular reaction) or the benzyl amide resulting from the transamidation of the Weinreb amide 16 (intramolecular reaction). 17 According to the stereochemical outcome of the reaction, regardless of the nucleophile, the addition to the trifluoromethyl ketone would happen via the Felkin-Anh transition state TS-2, 18,19 as shown in Figure 1. Cyclization toward hemiaminals 4a−c is made possible thanks to the syn stereochemical relationship of the acetonide-protected diol.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The aza nucleophile could be the benzyl amine (intermolecular reaction) or the benzyl amide resulting from the transamidation of Weinreb amide 16 (intramolecular reaction). 17 According to the stereochemical outcome of the reaction, regardless the nucleophile, addition to the trifluoromethyl ketone would happen via the Felkin-Anh transition state TS-2, 18,19 as shown in Having developed a short and highly efficient synthesis of enantiopure atrifluoromethylated N,O-acetals having a cis-diol motif, we envisaged to use this reaction sequence to prepare original N-acyliminium ions precursors allowing to study diastereoselective Pictet-Spengler cyclization. The required starting N,O-acetals 5a-g were easily prepared by reacting the hydrated ketone 3 with 2 equiv of variously substituted phenethylamines or the 1-methyltryptamine at reflux of toluene (Table 3).…”

Section: Resultsunclassified

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cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions

et al. 2020

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The synthesis of cyclic, chiral α-trifluoromethylated N,O-acetals having a protected cis-diol moiety has been readily achieved in two steps from a known bis-Weinreb amide derived from l-tartaric acid. The reaction of O-acetyl analogues of these N,O-acetals with triflic acid in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) at 0 °C generated in situ the corresponding electrophilic α-trifluoromethyl N-acyliminium ions that undergo Pictet-Spengler-type cyclizations. After only 10 min of reaction, the original enantiopure aza-tricyclic scaffolds bearing a trifluoromethyl substituent at the bridgehead position were obtained with diastereoselectivities ranging from 75:25 to 97:3.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsunclassified

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cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions

et al. 2020

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One‐Step Nickel‐Catalyzed Synthesis of Alpha‐Arylidene and Gamma Hydroxy‐Substituted N‐Methyl‐2‐Pyrrolidones

Sirvin Rajan,

Mok,

Lee

et al. 2024

Asian J Org Chem

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This study describes a method to synthesize compounds with an arylidene group at the alpha position of N‐methyl‐2‐pyrrolidone (NMP) and an alcohol group at the gamma position in a single‐step reaction using NMP and an aldehyde. The highest yields were obtained with Ni(glyme)Cl2 as a nickel catalyst and tert‐butyl hydroperoxide as the oxidant, and various aryl aldehydes reacted under optimal conditions to yield the target compounds.

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Pyridazines and Their Benzo Derivatives

Chinigo

Feng

Hoy

et al. 2022

Comprehensive Heterocyclic Chemistry IV

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Divergent pathways for reactions of CF3-containing Isobenzofuran-1-ones and amines

Cited by 6 publications

References 25 publications

cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions

cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions

One‐Step Nickel‐Catalyzed Synthesis of Alpha‐Arylidene and Gamma Hydroxy‐Substituted N‐Methyl‐2‐Pyrrolidones

Pyridazines and Their Benzo Derivatives

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