0000000000805793

AUTHOR

Dirk Schanzenbach

showing 2 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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