Synthesis and characterization of fluorous (S)- and (R)-1-phenylethylamines that effect heat facilitated resolution of (±)-2-(8-carboxy-1-naphthylsulfinyl)benzoic acid via diastereomeric salt formation and study of their circular dichroism

摘要: Abstract Perfluoroalkyl- or nonafluoro- tert -butoxy-alkyl-substituted enantiopure amines having the structure PhCHCH 3 (NR 1 R 2 ) [R  = H, CH ;  = (CH C 8 F 17 , (CH OC(CF  = R ] are obtained in high yields, when ( S )-(−)-1-phenylethylamine is reacted with readily accessible alkylating reagents fluorous 2° (R  = H; methylated a Leuckart–Wallach reaction. The solubility patterns of these novel chiral and their hydrochlorides qualitatively described for broad spectrum solvents partition coefficients free bases determined by GC. A method resolution enantiomers disclosed here, which involves use half-equivalent selected resolving agent solvent water that displays low crystalline diastereomeric salt(s) formed even at temperatures near to its boiling point. Compound )-(−)-PhCHCH [NH(CH found satisfy all latter conditions successfully used heat facilitated title racemic acid. circular dichroism (CD) spectra six derivatives measured ethanol, trifluoroethanol hexafluoropropan-2-ol discussed detail.