6533b834fe1ef96bd129d579

RESEARCH PRODUCT

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

Dirk SchanzenbachWaldemar PfrengleHorst KunzWilfried Sager

subject

GlycosylamineNitrileStereochemistryOrganic ChemistryStrecker amino acid synthesisDiastereomerBiochemistryMedicinal chemistryAsymmetric inductionchemistry.chemical_compoundchemistryDrug DiscoveryAmine gas treatingLewis acids and basesTetrahydrofuran

description

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.

https://doi.org/10.1016/s0040-4039(00)80504-3