title: 2,2'-Dihydroxybenzil: a stereodynamic probe for primary amines controlled by steric strain.
abstract: A rational approach for generating 1,1'-binaphthalene-like axial chirality of a small organic receptor, 2,2'-dihydroxybenzil is presented. The receptor combines with 2 equiv of monodentate primary amines to form a diimine, of which axial chirality is controlled by steric strain with moderate (1.4:1) to good (4.7:1) stereoselectivity. The observed circular dichroism (CD) spectra have been closely simulated by TD-DFT computations and can be used for determining the absolute chirality and enantiomeric excess of primary amines.
authors.affiliation: Department of Chemistry, KAIST , Daejeon 305-701, Korea.
authors.forename: Min-Seob
authors.initials: MS
authors.lastname: Seo
authors.forename: Ansoo
authors.initials: A
authors.lastname: Lee
authors.forename: Hyunwoo
authors.initials: H
authors.lastname: Kim
mesh_terms: D000588:Amines / Q000737:chemistry*; D002942:Circular Dichroism; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: C000591958:2,2'-dihydroxybenzil; D000588:Amines; D009281:Naphthalenes; D010658:Phenylglyoxal