Synthesis by carbonate aminolysis and chiral recognition ability of cellulose 2,3-bis(3,5-dimethylphenyl carbamate)-6-(?-phenylethyl carbamate) selectors

Abstract Novel chiral selectors based on cellulose 2,3- bis (3,5-dimethylphenyl carbamate)-6-( ? -phenylethyl carbamate) were regioselectively synthesized by carbonate aminolysis and isocyanate chemistry. By oxycarbonylation with phenyl chloroformate, carbamoylation 3,5-dimethylphenyl isocyanate, subsequent of the previously introduced reactive moiety at C6 enantiopure ( R )-or S )- -phenylethylamine, have been obtained, which carry two different carbamate substituents. The derivatives comprehensively characterized ATR-FTIR, solid-state NMR, GPC, elemental analysis. In parallel, 3-aminopropyl-functionalized silica gel as an inert carrier material for was prepared obtained coated-type stationary phases both 29 Si 13 C enantioseparation performance studied compared to tris a reference. With this protocol in hand, certain shortcomings conventional approaches towards regioselective synthesis polysaccharide-based overcome, such limitation standard reagents, being able apply now whole wealth commercially available (chiral) primary also secondary alkylamines instead. Graphical abstract