title: Enantioselective recognition of 1,2-amino alcohols by reversible formation of imines with resonance-assisted hydrogen bonds.
abstract: A chiral aldehyde with three H-bond donating groups (2) has been synthesized. This aldehyde binds a variety of chiral 1,2-amino alcohols in benzene with the same sense of stereoselectivity. Computational and experimental data indicate that one imine bond, one resonance-assisted H-bond to the imine nitrogen, and two H-bonds to the alcoholic oxygen all play an important role in the stereoselective recognition. [structure: see text]
authors.affiliation: Department of Chemistry, Division of Nano Sciences, and Center for Biomimetic Systems, Ewha Womans University, Seoul 120-750, South Korea. kkmook@ewha.ac.kr
authors.forename: Kwan Mook
authors.initials: KM
authors.lastname: Kim
authors.forename: Hyunjung
authors.initials: H
authors.lastname: Park
authors.forename: Hae-Jo
authors.initials: HJ
authors.lastname: Kim
authors.forename: Jik
authors.initials: J
authors.lastname: Chin
authors.forename: Wonwoo
authors.initials: W
authors.lastname: Nam