title: Configurationally labile enantioenriched lithiated 3-arylprop-2-enyl carbamates: joint experimental and quantum chemical investigations on the equilibrium of epimers.
abstract: Experimental investigations as well as high-level quantum chemical calculations are performed on the two epimeric pairs of complexes 4.2 and 6.2 obtained by lithiation of cinnamyl carbamate (1) and 1-naphthyl derivative 5 in the presence of BOX ligands (S,S)- and (R,R)-2. Indeed, in the case of configurationally labile complexes and a dynamic thermodynamic resolution, which is found to take place, one of both epimers is energetically favored. The quantum chemical computations allow the prediction of the enantiomeric excess that can be expected.
authors.affiliation: Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Germany.
authors.forename: Thérèse
authors.initials: T
authors.lastname: Hémery
authors.forename: Robert
authors.initials: R
authors.lastname: Huenerbein
authors.forename: Roland
authors.initials: R
authors.lastname: Fröhlich
authors.forename: Stefan
authors.initials: S
authors.lastname: Grimme
authors.forename: Dieter
authors.initials: D
authors.lastname: Hoppe
mesh_terms: D002219:Carbamates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D002219:Carbamates; D009942:Organometallic Compounds; D008094:Lithium