Synthesis, resolution, and absolute configuration determination of a vicinal amino alcohol with axial chirality. Application to the synthesis of new box and pybox ligands

Lopez-Ram-de-Viu, Pilar (Universidad de Zaragoza) ; Galvez, Jose A. (Universidad de Zaragoza) ; Diaz-de-Villegas, Maria D.

Resumen: New racemic vicinal amino alcohol derivatives with 4-benzylidenecyclohexane skeleton and axial chirality have been prepared. A preparatively easy and efficient protocol for resolution of the N-benzoylamino alcohol is described. Using a 250 x 20 mm (L x ID) Chiralpak (R) IA column, and the appropriate mixture of n-hexane/ethanol/chloroform as eluent, both enantiomers of N-benzoylamino alcohol 3 are obtained with >99% enantiomeric excess (ee) by successive injections of a solution of the racemic sample in chloroform. The obtained axially chiral vicinal amino alcohol is used to synthesize structurally novel bisoxazoline ligands in high yields.

Idioma: Inglés

DOI: 10.1002/chir.23475

Año: 2022

Publicado en: Chirality 34, 8 (2022), 1140-1150
ISSN: 0899-0042

Factor impacto JCR: 2.0 (2022)

Categ. JCR: CHEMISTRY, ORGANIC rank: 30 / 52 = 0.577 (2022) - Q3 - T2
Categ. JCR: CHEMISTRY, ANALYTICAL rank: 59 / 86 = 0.686 (2022) - Q3 - T3
Categ. JCR: PHARMACOLOGY & PHARMACY rank: 218 / 278 = 0.784 (2022) - Q4 - T3
Categ. JCR: CHEMISTRY, MEDICINAL rank: 47 / 60 = 0.783 (2022) - Q4 - T3

Factor impacto CITESCORE: 3.7 - Pharmacology, Toxicology and Pharmaceutics (Q3) - Chemistry (Q3) - Chemical Engineering (Q3)

Factor impacto SCIMAGO: 0.382 - Analytical Chemistry (Q3) - Catalysis (Q3) - Spectroscopy (Q3) - Organic Chemistry (Q3) - Pharmacology (Q3) - Drug Discovery (Q3)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E45-20R

Tipo y forma: Article (Published version)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)