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Double Asymmetric Hydrogenation of Linear β,β-Disubstituted α,β-Unsaturated Ketones into γ-Substituted Secondary Alcohols using a Dual Catalytic System
- Source :
- Chemistry - A European Journal. 23(37):8806-8809
- Publication Year :
- 2017
- Publisher :
- Wiley, 2017.
-
Abstract
- Double asymmetric hydrogenation of linear β,β-disubstituted α,β-unsaturated ketones catalyzed by the DM-SEGPHOS/DMAPEN/RuII complex with t-C4H9OK afforded the γ-substituted secondary alcohols in high diastereo- and enantioselectivities. Some mechanistic experiments suggested that two different reactive species, type (I) and (II), were reversibly formed in this catalytic system: Type (I) with the diamine ligand DMAPEN enantioselectively hydrogenated the enones into the chiral allylic alcohols, and type (II) without the diamine ligand diastereoselectively hydrogenated the allylic alcohols into the γ-substituted secondary alcohols. This dual catalysis protocol was successfully applied to the reaction of a variety of aliphatic- and aromatic-substituted enone substrates.
- Subjects :
- Allylic rearrangement
010405 organic chemistry
Chemistry
Ligand
Organic Chemistry
Asymmetric hydrogenation
Enantioselective synthesis
Noyori asymmetric hydrogenation
General Chemistry
010402 general chemistry
01 natural sciences
Medicinal chemistry
Catalysis
0104 chemical sciences
chemistry.chemical_compound
Diamine
Enone
Subjects
Details
- Language :
- English
- ISSN :
- 09476539
- Volume :
- 23
- Issue :
- 37
- Database :
- OpenAIRE
- Journal :
- Chemistry - A European Journal
- Accession number :
- edsair.doi.dedup.....f30c8f211978d13e863f30f7ab37d8f0