Unknown

Dataset Information

0

Catalytic asymmetric ?-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 ?-hydroxy imines to ?-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.

SUBMITTER: Zhang X 

PROVIDER: S-EPMC4195388 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

altmetric image

Publications

Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.

Zhang Xin X   Staples Richard J RJ   Rheingold Arnold L AL   Wulff William D WD  

Journal of the American Chemical Society 20140923 40


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 diffracti  ...[more]

Similar Datasets

| S-EPMC2966826 | biostudies-other
| S-EPMC7955048 | biostudies-literature
| S-EPMC7580270 | biostudies-literature
| S-EPMC8873952 | biostudies-literature
| S-EPMC2947798 | biostudies-literature
| S-EPMC6541354 | biostudies-literature
| S-EPMC4878850 | biostudies-literature
| S-EPMC7910428 | biostudies-literature
| S-EPMC397407 | biostudies-literature
| S-EPMC4661081 | biostudies-literature