Copper-Catalyzed Asymmetric Sulfonylative Desymmetrization of Glycerol

Glycerol is the main side product in the biodiesel manufacturing process, and the development of glycerol valorization methods would indirectly contribute the sustainable biodiesel production and decarbonization. Transformation of glycerol to optically active C3 units would be one of the attractive...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-12, Vol.27 (24), p.9025
Main Authors: Yamamoto, Kosuke, Miyamoto, Keisuke, Ueno, Mizuki, Takemoto, Yuki, Kuriyama, Masami, Onomura, Osamu
Format: Article
Language:English
Subjects:
Analysis
asymmetric reaction
Asymmetry
Biodiesel fuels
Biofuels
Catalysis
Catalysts
Ceramide
Chemical reactions
Climate change
Copper
copper catalysis
desymmetrization
Diesel
Enantiomers
Glycerin
Glycerol
Identification and classification
Kinases
Ligands
Manufacturing industry
Methods
Properties
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Summary:Glycerol is the main side product in the biodiesel manufacturing process, and the development of glycerol valorization methods would indirectly contribute the sustainable biodiesel production and decarbonization. Transformation of glycerol to optically active C3 units would be one of the attractive routes for glycerol valorization. We herein present the asymmetric sulfonylative desymmetrization of glycerol by using a CuCN/( , )-PhBOX catalyst system to provide an optically active monosulfonylated glycerol in high efficiency. A high degree of enantioselectivity was achieved with a commercially available chiral ligand and an inexpensive carbonate base. The optically active monosulfonylated glycerol was successfully transformed into a C3 unit attached with differentially protected three hydroxy moieties. In addition, the synthetic utility of the present reaction was also demonstrated by the transformation of the monosulfonylated glycerol into an optically active synthetic ceramide, sphingolipid E.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27249025