0000000000777097

AUTHOR

Isabelle Netz

showing 3 related works from this author

Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles.

2015

A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.

chemistry.chemical_classificationAlkylationMolecular StructureChemistryOrganic ChemistryStrecker amino acid synthesisEnantioselective synthesisStereoisomerismAlkylationCatalysislaw.inventionAmino acidDioxanesDeprotonationlawNitrilesOrganic chemistryCrystallizationAmino AcidsProtonsEnantiomeric excessThe Journal of organic chemistry
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ChemInform Abstract: Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles.

2015

An α-alkylation of deprotonated α-amino nitriles, prepared from chiral phenyldioxanamine (I) by Strecker reaction, leads to α-quaternary arylglycines with high optical purity after hydrolysis and oxidative cleavage of the chiral auxiliary.

chemistry.chemical_classificationChiral auxiliarychemistry.chemical_compoundHydrolysisDeprotonationchemistryStrecker amino acid synthesisEnantioselective synthesisGeneral MedicineAlkylationEnantiomeric excessMedicinal chemistryAmino acidChemInform
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(1-Adamantyl)methyl glycidyl ether: a versatile building block for living polymerization.

2014

(1-Adamantyl)methyl glycidyl ether (AdaGE) is introduced as a versatile monomer for oxyanionic polymerization, enabling controlled incorporation of adamantyl moieties in aliphatic polyethers. Via copolymerization with ethoxyethyl glycidyl ether (EEGE) and subsequent cleavage of the acetal protection groups of EEGE, hydrophilic linear polyglycerols with an adjustable amount of pendant adamantyl moieties are obtained. The adamantyl unit permits control over thermal properties and solubility profile of these polymers (LCST). Additionally, AdaGE is utilized as a termination agent in carbanionic polymerization, affording adamantyl-terminated polymers. Using these structures as macroinitiators fo…

chemistry.chemical_classificationGlycerolMaterials sciencePolymers and PlasticsEthylene oxidePolymersOrganic ChemistryAcetalAdamantanePolymerPolymerizationchemistry.chemical_compoundMonomerchemistryPolymerizationPolymer chemistryAmphiphileMaterials ChemistryCopolymerLiving polymerizationOrganic chemistryEpoxy CompoundsHydrophobic and Hydrophilic InteractionsMacromolecular rapid communications
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