AI Article Synopsis
- Amphiphilic fluorocarbons are materials that can easily self-assemble and stick to both inorganic and biological surfaces, but their complex synthesis has limited their applications.
- A new method is described for synthesizing a specific fluorocarbon compound, achieving a high yield of one diastereomer without needing purification.
- The synthesis involves trimerizing trifluoroacetone with a catalyst, and studies showed that the process is reversible, leading to the formation of the most stable compound by adjusting the temperature.
Article Abstract
Amphiphilic fluorocarbons have unique properties that facilitate their self assembly and adhesion to both inorganic and biological substrates. Incorporation of these moieties into valuable constructs typically require complex synthetic routes that have limited their use. Here, the base-catalyzed diastereoselective synthesis of 6-methyl-2,4,6-tris(trifluoromethyl)tetrahydro-2H-pyran-2,4-diol is reported. Trimerization of trifluoroacetone in the presence of 5 mol% KHMDS delivers one of four diastereomers selectively in 81% yield with no column chromatography. Temperature screening revealed the reversibility of this trimerization and the funneling of material into the most thermodynamically stable oxane. Subsequent functionalization with boronic acids is reported.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5584686 | PMC |
| http://dx.doi.org/10.1039/c7ob01094j | DOI Listing |
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