Chiral Recognition of 1,1′-Bi-2-naphthol Enantiomers by Twisted Amidine Derivatives: Rational Design of a Highly Enantioselective Receptor

Abstract Clarification of the molecular structures of diastereomeric complexes relevant to the enantioselective dual N···HO binding between the chiral C 2 amidine derivative (S,S)- 1 and 1,1′-bi-2-naphthol 2 in CDCl 3 afforded the structural factor determining the sense of observed enantioselection. This insight into chiral recognition was successfully applied to the design of a new twisted dual hydrogen bond acceptor (S,S)- 3 that exhibited a higher level of enantioselectivity toward 2 .