Expeditious preparation of β-sec-alkyl vicinal amino alcohols used for chiral ligand synthesis

Abstract

An economic route providing quick access to chiral β-amino alcohols bearing one β-sec-alkyl was developed. This protocol starts with commercially available and cheap chiral source such as derivatives of L-serine...

Brønsted-Acid-Catalyzed Enantioselective Desymmetrization of 1,3-Diols: Access to Chiral β-Amino Alcohol Derivatives

“…Chiral β-amino alcohols are important structural motifs found in numerous natural products, pharmaceuticals, and biologically active molecules (Figure ), such as metaraminol, bestatin, sphingolipids, and thiamphenicol . The bifunctional amino alcohol moieties have also been employed as versatile synthons for the assembly of chiral catalysts, ligands, and auxiliaries . Typically, chiral β-amino alcohols are prepared through asymmetric hydrogenation, asymmetric nucleophilic addition onto imines or ketones, asymmetric aminohydroxylation of alkenes, asymmetric ring opening of epoxides or aziridines, and asymmetric radical coupling .…”