The bidentate complexes of (R,R)- and meso-α,α′-bis(trifluoromethyl)-9,10-anthracenedimethanol with cis-1-amino-2-indanol

cis-1-Amino-2-indanol in Drug Design and Applications to Asymmetric Processes

“…When 1 equiv of 22 on a 3:1 mixture of (1 R ,2 S )- 1 and (1 S ,2 R )- 1 was used, mean differentiation was observed for H 1 and H 3 . Protons H 3 cis and H 3 trans are more shielded in (1 S ,2 R )- 1 , while H 1 in (1 R ,2 S )- 1 is the most shifted to higher fields . Virgili and co-workers later found that ( R , R )- 23 gave similar enantiodiscrimination as ( R , R )- 22 , but ( R , R )- 23 also enantiodifferentiates nuclei not separated by ( R , R )- 22 , for example, the signal of H 2 …”

“…Virgili and co-workers studied the enantiorecognition of cis -aminoindanol by ( R , R )-α,α ‘ -bis(trifluoromethyl)-9,10-anthracenedimethanol 22 . The examination of the bidentate associations between 22 and 1 revealed that the cisoid conformation of 22 is responsible for the separation of the NMR signals.…”

A New Chirally Organized Trifluoromethylanthrylmethanol Derivative and Its Application as Chiral Solvating Agent

“…Although it is difficult to generalize, the enlargement of the enantiodistinctive capacity of a CSA depends basically on the uprightness of the incorporated structural modifications, such as the introduction of more stereogenic centres, the increase of aromatic surface, and the modification of steric hindrance . These cited factors encourage the eventual formation of two different diastereoisomeric complexes between the CSA and the chiral substrate, based on their different geometry and/or binding constants.…”

Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl Muconate: A Highly Chiral Cavity for Enantiodiscrimination by NMR

“…The new compound would be formed by two aromatic chiral molecules, α,α‘-(bistrifluoromethyl)-9,10-anthracenedimethanol 1 (ABTE), bonded and separated by a spacer, which would allow a chiral cavity to be formed. α,α‘-(Bistrifluoromethyl)-9,10-anthracenedimethanol has been proven to be a highly effective CSA because of the presence of two chiral groups which contain acidic hydroxyl groups that are capable of forming two hydrogen bonds with the substrate at the same time . Similarly, the target molecule will have two chiral hydroxyl groups, and its concave−convex topology will also optimize the interactions with the solute.…”