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Journal article
Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
Chemical science (Cambridge), Vol.9(11), pp.2975-2980
2018
PMID: 29719678
Web of Science ID: WOS:000431100800013
Abstract
Herein, we report a Zn-ProPhenol catalyzed direct asymmetric amination reaction of unactivated aryl and vinyl ketones using di-tert-butyl azodicarboxylate as a cheap and practical electrophilic nitrogen source. Importantly, this methodology works with both α-branched and unbranched ketones for the construction of tri- and tetrasubstituted N-containing stereocenters. The reaction can be run at gram-scale with low catalyst loadings and features a recoverable and reusable ligand. Finally, the enantioenriched hydrazine products can be readily converted into versatile building blocks such as α-amino carbonyl compounds and β-amino alcohols.
Details
- Title
- Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters
- Publication Details
- Chemical science (Cambridge), Vol.9(11), pp.2975-2980
- Resource Type
- Journal article
- Publisher
- Royal Society of Chemistry
- Grant note
- R01 GM033049 / NIGMS NIH HHS
- Copyright
- © The Royal Society of Chemistry 2018
- Identifiers
- WOS:000431100800013; 99381709174406600
- Academic Unit
- Chemistry; Hal Marcus College of Science and Engineering
- Language
- English