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Catalytic Asymmetric α‑Iminol Rearrangement: New Chiral Platforms

Zhang, Xin ; Staples, Richard J ; Rheingold, Arnold L ; Wulff, William D

Journal of the American Chemical Society, 2014-10, Vol.136 (40), p.13971-13974 [Periódico revisado por pares]

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Título:
Catalytic Asymmetric α‑Iminol Rearrangement: New Chiral Platforms
Autor: Zhang, Xin ; Staples, Richard J ; Rheingold, Arnold L ; Wulff, William D
Assuntos: Asymmetry ; Catalysis ; Catalysts ; Communication ; Diffraction ; Imines - chemistry ; Ligands ; Models, Molecular ; Molecular Conformation ; Platforms ; Stereoisomerism ; X-rays ; Zirconium
É parte de: Journal of the American Chemical Society, 2014-10, Vol.136 (40), p.13971-13974
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: 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.
Editor: United States: American Chemical Society
Idioma: Inglês

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