Novel Chiral Stationary Phases for the Resolution of the Enantiomers of Amino Acids by Ligand Exchange Chromatography

Abstract

Novel chemically bonded chiral stationary phases (CSP’s) derived from (1R,2S)-2-carboxymethylamino-1,2-diphenylethanol and from (1S,2S)-2-carboxymethylamino-1,2-diphenylethanol were prepared. The ligand exchange chromatography on these CSP’s was found to be effective for the direct resolution of the enantiomers of amino acids.

Asymmetric Synthesis of [2,3-13C2,15N]-4-Benzyloxy-5,6-diphenyl-2,3,5,6-tetrahydro-4H-oxazine-2-one via Lipase TL-Mediated Kinetic Resolution of Benzoin: General Procedure for the Synthesis of [2,3-13C2,15N]-l-Alanine

“…To synthesize oxazinones 4a and 4b , it is necessary to prepare erythro -2-amino-1,2-diphenylethanol 3a and 3b in optically pure form. The preparation of the optically pure amino alcohols 3a and 3b has recently received widespread attention due to the use of these amino alcohols as chiral auxiliaries in asymmetric synthesis, chiral stationary phase for HPLC applications, and ligands in asymmetric catalysis . Several methods have been described in the literature for the synthesis of both antipodes of amino alcohols 3a and 3b .…”

Stereocontrolled Reactions Mediated by a Remote Sulfoxide Group: Synthesis of Optically Pure anti-β-Amino Alcohols

“…Enantiomerically pure β-amino alcohols are structural subunits of wide occurrence in natural products. These compounds are of importance as key synthetic intermediates for the synthesis of biologically active compounds and as stationary phases in HPLC . However, the main interest in these substrates is related to their use as chiral ligands or auxiliaries in asymmetric reactions .…”

Single Route to Chiral syn- and anti-2-Amino-1,2-diphenylethanols via a New Stereodivergent Opening of trans-1,2-Diphenyloxirane

“…β-Amino alcohol subunits, since their discovery in many biologically active compounds, especially as α-amino-β-hydroxy or α-hydroxy-β-amino acids, have attracted the attention of synthetic chemists, and several approaches to the synthesis of these units have now been developed . Among this class of compounds, the 2-amino-1,2-diphenylethanols, with both syn and anti relative configurations (compounds 1 and 2 , respectively, in Figure ), have recently received great attention due to their use, in optically active forms, as chiral auxiliaries in asymmetric synthesis, chiral stationary phases for HPLC, and chiral ligands in asymmetric catalysis 1 …”