Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 2, Pages 355-363Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001224
Keywords
Organofluorine chemistry; Fluorohydrins; Conformation analysis; Enantioselectivity; Nucleophilic substitution; Quantum chemical calculations
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Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 424]
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Selective syntheses of enantiopure regio- and diastereomeric methyl 2,3-fluoro-hydroxyalkanoates via four different routes employing two types of fluorination reagents are reported. The anti- and syn-3-fluoro-2-hydroxyalkanoates 1 and 3 were prepared by treating the corresponding epoxides with Olah's reagent (Py.9HF). Cyclic sulfates prepared from the enantiomeric diols were ring-opened with TBAF to give the anti- and syn-2-fluoro-3-hydroxyalkanoates 2 and 4. The stereochemical analysis was performed mainly by NMR spectroscopy. Applying DFT/B3LYP and SCS-MP2 quantum chemical methods, the coupling constants and relative energies of conformers were calculated. Solvent effects were considered using the COSMO continuum model.
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