- Towards Enzyme-like, Sustainable Catalysis: Switchable, Highly Efficient Asymmetric Synthesis of Enantiopure Biginelli Dihydropyrimidinones or Hexahydropyrimidinones
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Organocatalysts displaying a network of cooperative hydrogen bonds (NCHB) have been employed in an enzyme-like manner for a direct, switchable synthesis of enantiopure hexahydropyrimidinones (HHPMs) or dihydropyrimidinones (DHPMs), which starts at a common, easily accessible α-ureidosulfone stage. The NCHB organocatalyst exploits all its potential as a pure hydrogen-bond biomimetic catalyst even in the presence of organic bases. This one-pot, diastereo- and enantioselective synthetic procedure has been proven to be robust, scalable, highly efficient, and environmentally benign. A straightforward and truly practical entry to enantiopure HHPMs is reported for the first time.
- Lillo,Saá
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supporting information
p. 17182 - 17186
(2016/11/23)
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- A new approach to the synthesis of Biginelli compounds
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A new synthesis of 4-aryl-2-oxo-l,2,3,4-tetrahydropyrimidine-5-carboxylic acid esters is based on the reactions of α-tosyl-substituted phenyl carbamates with the enolates of β-oxoesters followed by treatment with ammonia and dehydration of the resulting 4
- Shutalev, Anatoly D.,Kurochkin, Nikolay N.
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