title: Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.
abstract: A series of 19 different asymmetric catalysts were screened in an effort to identify the first chiral catalyst for the rearrangement of α-hydroxy imines to α-amino ketones involving a 1,2-carbon shift. Although aluminate complexes of VAPOL, VANOL, and 7,7'-(t)Bu2VANOL were quite effective catalysts giving up to 88% ee, the ne plus ultra catalyst for this reaction was found to be a zirconium complex of VANOL which gives 97 to >99% ee for the majority of the substrates examined. An X-ray diffraction study of the catalyst reveals that the zirconium exists as a homoleptic complex with three VANOL ligands and two protonated N-methyl imidazoles.
authors.affiliation: Department of Chemistry, Michigan State University , East Lansing, Michigan 48824, United States.
authors.forename: Xin
authors.initials: X
authors.lastname: Zhang
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Staples
authors.forename: Arnold L
authors.initials: AL
authors.lastname: Rheingold
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
mesh_terms: D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007097:Imines