6533b854fe1ef96bd12ae7d6
RESEARCH PRODUCT
ChemInform Abstract: Reversal of Asymmetric Induction in Stereoselective Strecker Synthesis on Galactosyl Amine as the Chiral Matrix.
Waldemar PfrengleHorst KunzWilfried SagerDirk Schanzenbachsubject
chemistry.chemical_compoundchemistryStrecker amino acid synthesisDiastereomerStereoselectivityAmine gas treatingGeneral MedicineLewis acids and basesMedicinal chemistryAsymmetric inductionTetrahydrofuranCatalysisdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1989-02-28 | ChemInform |