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

ABSTRACT: 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 × 20 mm (L × ID) Chiralpak® 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.

SUBMITTER: Lopez-Ram-de-Viu P 

PROVIDER: S-EPMC9545338 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature