876478-10-3Relevant articles and documents
Catalytic asymmetric α-iminol rearrangement: New chiral platforms
Zhang, Xin,Staples, Richard J.,Rheingold, Arnold L,Wulff, William D.
, p. 13971 - 13974 (2014/12/10)
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'-tBu2VANOL 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.
