6533b834fe1ef96bd129d579
RESEARCH PRODUCT
Reversal of asymmetric induction in stereoselective strecker synthesis on galactosyl amine as the chiral matrix
Dirk SchanzenbachWaldemar PfrengleHorst KunzWilfried Sagersubject
GlycosylamineNitrileStereochemistryOrganic ChemistryStrecker amino acid synthesisDiastereomerBiochemistryMedicinal chemistryAsymmetric inductionchemistry.chemical_compoundchemistryDrug DiscoveryAmine gas treatingLewis acids and basesTetrahydrofurandescription
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 |
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1988-01-01 | Tetrahedron Letters |