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Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of α-Alkyl-β-Ketoaldehydes via Dynamic Kinetic Resolution
- Source :
- Molecules, Vol 29, Iss 14, p 3420 (2024)
- Publication Year :
- 2024
- Publisher :
- MDPI AG, 2024.
-
Abstract
- The (R,R)-Teth-TsDPEN-Ru(II) complex promoted the one-pot double C=O reduction of α-alkyl-β-ketoaldehydes through asymmetric transfer hydrogenation/dynamic kinetic resolution (ATH-DKR) under mild conditions. In this process, ten anti-2-benzyl-1-phenylpropane-1,3-diols (85:15 to 92:8 dr) were obtained in good yields (41–87%) and excellent enantioselectivities (>99% ee for all compounds). Notably, the preferential reduction of the aldehyde moiety led to the in situ formation of 2-benzyl-3-hydroxy-1-phenylpropan-1-one intermediates. These intermediates played a crucial role in enhancing both reactivity and stereoselectivity through hydrogen bonding.
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 29
- Issue :
- 14
- Database :
- Directory of Open Access Journals
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.86fd507be1104d1fa9c0ae47677d00df
- Document Type :
- article
- Full Text :
- https://doi.org/10.3390/molecules29143420