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Journal article
Asymmetric Electrophilic Amination and Hydrazination of Acyclic α-Branched Ketones for the Formation of α-Tertiary Amines and Hydrazines
ACS catalysis, Vol.9(12), pp.11082-11087
12/06/2019
Web of Science ID: WOS:000502169900043
Abstract
Chiral alpha-tertiary amines can be accessed directly through the electrophilic amination of alpha-branched ketones utilizing di-tert-butyl azodicarboxylate as the electrophilic nitrogen source. This process, catalyzed by a dinuclear zinc-ProPhenol complex, proceeds under mild reaction conditions and with a diverse range of vinyl ketones. The reactions can be run on gram-scale with reduced catalyst loadings and feature a recoverable ligand. The hydrazine products are shown to undergo chemoselective N-N bond cleavage without reduction of the alpha,beta-unsaturated ketone, revealing chiral alpha-amino ketones.
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Details
- Title
- Asymmetric Electrophilic Amination and Hydrazination of Acyclic α-Branched Ketones for the Formation of α-Tertiary Amines and Hydrazines
- Publication Details
- ACS catalysis, Vol.9(12), pp.11082-11087
- Resource Type
- Journal article
- Publisher
- American Chemical Society
- Number of pages
- 11
- Grant note
- Tamaki Foundation Chugai Pharmaceuticals Stanford Chemistry Department Summer Research Fellowship
- Copyright
- © 2019 American Chemical Society
- Identifiers
- WOS:000502169900043; 99381709285906600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English