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Synthesis, resolution, and absolute configuration determination of a vicinal amino alcohol with axial chirality. Application to the synthesis of new box and pybox ligands
Author(s) -
LópezRamdeVíu Pilar,
Gálvez José A.,
DíazdeVillegas María D.
Publication year - 2022
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23475
Subject(s) - vicinal , chemistry , enantiomer , chloroform , chirality (physics) , alcohol , absolute configuration , enantiomeric excess , ethanol , axial chirality , hexane , resolution (logic) , stereochemistry , column chromatography , organic chemistry , enantioselective synthesis , catalysis , chiral symmetry breaking , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
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.