0000000000805794

AUTHOR

Wilfried Sager

showing 5 related works from this author

Reversal of asymmetric induction in stereoselective strecker synthesis on galactosyl amine as the chiral matrix

1988

Abstract The reversal of the direction of asymmetric induction in Lewis acid catalyzed Strecker synthesis using the 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl amine 1 is described. In isopropanol or tetrahydrofuran 1 had given ( R )-diastereomers of the corresponding α-amino nitriles preferably. However, in chloroform in the presence of heterogeneous zinc chloride the same auxiliary alternatively leads to an excess of the ( S )-diastereomers.

GlycosylamineNitrileStereochemistryOrganic ChemistryStrecker amino acid synthesisDiastereomerBiochemistryMedicinal chemistryAsymmetric inductionchemistry.chemical_compoundchemistryDrug DiscoveryAmine gas treatingLewis acids and basesTetrahydrofuranTetrahedron Letters
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ChemInform Abstract: Reversal of Asymmetric Induction in Stereoselective Strecker Synthesis on Galactosyl Amine as the Chiral Matrix.

1989

Abstract The reversal of the direction of asymmetric induction in Lewis acid catalyzed Strecker synthesis using the 2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl amine 1 is described. In isopropanol or tetrahydrofuran 1 had given ( R )-diastereomers of the corresponding α-amino nitriles preferably. However, in chloroform in the presence of heterogeneous zinc chloride the same auxiliary alternatively leads to an excess of the ( S )-diastereomers.

chemistry.chemical_compoundchemistryStrecker amino acid synthesisDiastereomerStereoselectivityAmine gas treatingGeneral MedicineLewis acids and basesMedicinal chemistryAsymmetric inductionTetrahydrofuranCatalysisChemInform
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ChemInform Abstract: Carbohydrates as Chiral Templates: Diastereoselective Ugi Synthesis of (S)-Amino Acids Using O-Acylated D-Arabinopyranosylamine …

1990

Abstract Enantiomerically pure (S)-amino acids are synthesized via a highly diastereoselective Ugi reaction using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine as the chiral template.

chemistry.chemical_classificationTemplateStereochemistryChemistryUgi reactionGeneral MedicineAmino acidChemInform
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Stereoselective glycosylation of Alcohols and Silyl Ethers Using Glycosyl Fluorides and Boron Trifluoride Etherate

1985

The stereoselective glycosylation of alcohols and their silyl ethers has been achieved using O-alkyl-, O-acyl-, and acetal-protected glycosyl fluorides of the pyranose and furanose series and boron trifluoride etherate in CH2Cl2.

inorganic chemicalschemistry.chemical_classificationanimal structuresGlycosylationSilylationChemistryOrganic ChemistryAlcoholEthermacromolecular substancesFuranoseBiochemistryCatalysiscarbohydrates (lipids)Inorganic Chemistrychemistry.chemical_compoundPyranoseDrug DiscoveryOrganic chemistrylipids (amino acids peptides and proteins)GlycosylPhysical and Theoretical ChemistryBoron trifluorideHelvetica Chimica Acta
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Carbohydrates as chiral templates: Diastereoselective Ugi synthesis of (S)-amino acids using O-acylated D-arabinopyranosylamine as the auxiliary

1989

Abstract Enantiomerically pure (S)-amino acids are synthesized via a highly diastereoselective Ugi reaction using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine as the chiral template.

chemistry.chemical_classificationGlycosylamineChemistryFormic acidStereochemistryIsocyanideOrganic ChemistryPhenylalanineBiochemistryAldehydeAmino acidchemistry.chemical_compoundDrug DiscoveryOrganic chemistryUgi reactionAliphatic compoundTetrahedron Letters
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