Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

Thiverny, Maryse; Farran, Daniel; Philouze, Christian; Blandin, Véronique; Chavant, Pierre Y.

doi:10.1016/j.tetasy.2011.07.022

Cited by 14 publications

(4 citation statements)

References 38 publications

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“…Preparation of Nitrones 1: Nitrones 1 were prepared by using a previously described sequence,18 starting from a glycine derivative and a ketone. The synthesis of 1b is reported below, the preparations of 1a 18b and 1c 16d have been described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

et al. 2014

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International audienceNew chiral nitroxides based on the imidazolidin-4-one skeleton, and the corresponding hydroxylamines, have been prepared from cyclic nitrones by a straightforward reaction sequence. They were evaluated as catalysts in the aerobic oxidation of benzyl alcohol using different co-catalysts. Both the imidazolidinone nitroxides and hydroxylamines were proven to catalyze the reaction, with the ring substituent having an effect depending on the co-catalytic system. In some cases, rapid oxidation to benzaldehyde was accomplished at room temperature under an atmospheric O2 pressure. Moreover, atroposelective desymmetrization was achieved during the aerobic oxidation of a diol catalyzed by an enantiopure imidazolidinone nitroxide. Finally, the electrochemical behavior of the new hydroxylamines and nitroxides was investigated by cyclic voltammetry, which gave insights into the observed catalytic properties

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Section: Methodsmentioning

confidence: 99%

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

et al. 2014

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“…To further illustrate the scope of this new tandem reaction toward other nucleophiles such as alkenes, we first evaluated the reaction using vinylmagnesium bromide . Unfortunately, the desired product was obtained in only 31% yield (Table , entry 1).…”

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confidence: 99%

Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction

et al. 2016

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A general and efficient synthesis of the 2H-tetrahydro-4,6-dioxo-1,2-oxazine ring system through a tandem nucleophilic addition and transesterification reaction is described. The reaction is highly functional-group-tolerant and proceeds under mild conditions, affording the corresponding products in good to excellent yields. This method represents the first general synthetic route to access this heterocyclic scaffold, which exists in the complex natural products alchivemycin A and B with significant antibiotic activities.

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“…The resulting monoprotected 5n was heated at 100 °C in 6 M HCl aqueous solution for 18 h . After ion-exchange column chromatography, phenylglycine ( 6n ) was obtained in 85% yield as white solids …”

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“…in 6 M HCl aqueous solution for 18 h. 18 After ion-exchange column chromatography, phenylglycine (6n) was in 85% yield as white solids. 19 A preliminary reaction mechanism of this carboxylation is proposed (Figure 2). Iminium formation from N-acyl-N,Oacetal is initiated by BF 3 .…”

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Synthesis of Arylglycines from CO₂ through α-Amino Organomanganese Species

2014

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In the presence of three readily available chemicals, Mn powder, BF3·OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding α-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free α-amino acids in two steps.

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Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

Cited by 14 publications

References 38 publications

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction

Synthesis of Arylglycines from CO₂ through α-Amino Organomanganese Species

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Totally diastereoselective addition of aryl Grignard reagents to the nitrone-based chiral glycine equivalent MiPNO

Cited by 14 publications

References 38 publications

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization

Access to the 2H-Tetrahydro-4,6-dioxo-1,2-oxazine Ring System from Nitrone via a Tandem Nucleophilic Addition and Transesterification Reaction

Synthesis of Arylglycines from CO2 through α-Amino Organomanganese Species

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Synthesis of Arylglycines from CO₂ through α-Amino Organomanganese Species