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2. Acid-Catalyzed Decomposition of

Author

Florian, Rouzier, Ophélie, Montiège, Jérôme, Lhoste, Catherine, Gaulon-Nourry, Anne-Sophie, Castanet, and Anne-Caroline, Chany

Abstract

Acid-catalyzed decomposition of diazocarbonyl compounds triggers a wide range of transformations leading to synthetically useful building blocks with high diversity. In this field, the chemistry of α-diazo-β-hydroxy ester substrates is largely dominated by migration processes. We describe herein a new approach to original mixed monosilyl acetals from

Published
2022

3. Synthesis of Constrained C-Glycosyl Amino Acid Derivatives Involving 1,3-Dipolar Cycloaddition of Cyclic Nitrone as Key Step

Author

Arnaud Martel, Florian Rouzier, Stéphane Guillarme, Gilles Dujardin, Rosanne Sillé, Arnaud Tessier, Arnaud Nourry, Muriel Pipelier, Ophélie Montiège, Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), and Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
C glycosides, chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Cycloaddition, 0104 chemical sciences, Amino acid, Nitrone, chemistry.chemical_compound, 1,3-Dipolar cycloaddition, [CHIM]Chemical Sciences, Glycosyl, Physical and Theoretical Chemistry
Abstract

International audience; An efficient two-step strategy for the synthesis of constrained C-glycosyl amino acid derivatives from C-vinylglycosides involving a 1,3-dipolar cycloaddition using L-(-)menthone-derived nitrone as the key step is described. After optimization of 1,3-dipolar cycloaddition conditions, various C-vinylglycosides were tested leading exclusively to one dia-[a]

Published
2020
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4. Practical Gram-Scale Synthesis of Either α- or β-Anomer of C-Vinyl Glycosides

Author

Arnaud Nourry, Florian Rouzier, Rosanne Sillé, Stéphane Guillarme, Arnaud Tessier, Muriel Pipelier, Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes - Faculté des Sciences et des Techniques, and Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)

Subjects
C glycosides, chemistry.chemical_classification, Anomer, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Organic Chemistry, Glycoside, Carbohydrate, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Organic chemistry, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, Gram
Abstract

The synthesis C-vinyl glycosides, useful intermediates for the synthesis of C-glycoconjugates, was carried out on gram-scale by controlled reduction of the corresponding ethynyl derivatives in good to excellent yields in different carbohydrate series.

Published
2019
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5. A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins

Author

Florian Rouzier, Fabien Boeda, Julien Caillé, Philippe Bertus, Morwenna S. M. Pearson-Long, Houcine Ammar, Fatma Boukattaya, Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculté des Sciences de Sfax, and Université de Sfax - University of Sfax

Subjects
chemistry.chemical_classification, amino acids, Grignard reagents, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Stereochemistry, Organic Chemistry, Nucleophilic acyl substitution, solvent effects, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Amino acid, Acylation, Reagent, Moiety, cyanohydrins, nitriles, Solvent effects, Chemoselectivity
Abstract

International audience; A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.

Published
2016
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6. ChemInform Abstract: A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins

Author

Philippe Bertus, Florian Rouzier, Fabien Boeda, Julien Caillé, Houcine Ammar, Fatma Boukattaya, and Morwenna S. M. Pearson-Long

Subjects
chemistry.chemical_classification, chemistry, Stereochemistry, Reagent, Moiety, General Medicine, Chemoselectivity, Amino acid
Abstract

A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.

Published
2016
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