New Approach to a Novel Axially Chiral Ligand Showing Spontaneous Enrichment of Axial Chirality

• Published in: Chemical & Pharmaceutical Bulletin Vol. 51; no. 3; pp. 265 - 267
• Main Authors: Hasegawa, Tomokuni, Omote, Masaaki, Sato, Kazuyuki, Ando, Akira, Kumadaki, Itsumaro
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 2003; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: biphenyl; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; chiral ligand; chirality enhancement; Exact sciences and technology; kinetic resolution; Life Sciences & Biomedicine; Ligands; Noncondensed benzenic compounds; Organic chemistry; Pharmaceutical Preparations - chemical synthesis; Pharmaceutical Preparations - chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; trifluorohydroxyethyl group; kinetic resolution; biphenyl; chiral ligand; trifluorohydroxyethyl group; chirality enhancement; Haloalcohol; Benzaldehyde; Organic ligand; Chiral compound; Haloketone; Asymmetric induction; Chemical reduction; Asymmetric reaction; Benzenic compound; Metalation; Fluorine Organic compounds; Ethylation; Secondary alcohol; Chemical synthesis
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.51.265

We have synthesized novel axially chiral ligand with two chiral centers, (R)-(R)2- and (S)-(S)2-2,2′-bis(2,2,2-trifluoro-1-hydroxyethyl)biphenyl (1), which showed a high asymmetric induction when used as ligand. Here, another new approach to 1 by kinetic and thermodynamic resolution is presented which gave these ligands in a much shorter steps, in a higher yield, and in a higher enantiomeric excess.