ArticleJournal of the American Chemical Society2014
Catalytic asymmetric α-Iminol rearrangement: new chiral platforms.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Intercepting an avoided α-iminol rearrangement with a Petasis reaction for the synthesis of 2,3-diaryl substituted indoles.Communications chemistry · 2025Article
- 1,2-Redox Transpositions of Tertiary Amides.Journal of the American Chemical Society · 2023Article
- Enantioselective synthesis of α-amino ketones through palladium-catalyzed asymmetric arylation of α-keto imines.Chemical science · 2022Article
- Zirconium-catalyzed asymmetric Kabachnik-Fields reactions of aromatic and aliphatic aldehydes.Chemical science · 2021Article
- Palladium-catalyzed benzylic C(spChemical science · 2021Article
- Green Chemistry Meets Asymmetric Organocatalysis: A Critical Overview on Catalysts Synthesis.ChemSusChem · 2021Review
- Recent development and applications of semipinacol rearrangement reactions.Chemical science · 2021Review
- Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.ACS central science · 2021Review
- α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions.Beilstein journal of organic chemistry · 2021Review
- Article
- A Nucleophilic Strategy for Enantioselective Intermolecular α-Amination: Access to Enantioenriched α-Arylamino Ketones.Journal of the American Chemical Society · 2015Article
- Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols.Nature communications · 2015Article
Corrections and comments
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Authors and funding
4 authors.
Funding
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.
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