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Beilstein J. Org. Chem. 2020, 16, 2141–2150, doi:10.3762/bjoc.16.182
Graphical Abstract
Figure 1: Examples of lipophilicity modulation for geminal dimethyl to cyclopropyl and oxetane modifications ...
Figure 2: Lipophilicity modulation examples involving fluorinated cyclopropane derivatives (measured experime...
Figure 3: Lipophilicity changes upon fluorination of isopropyl, cyclopropane and oxetane rings (Series A, C: ...
Figure 4: Lipophilicity modulations discussed in this contribution.
Figure 5: Distribution of the experimental lipophilicity values of series D, E and F (* denotes an estimated ...
Figure 6: Comparison of lipophilicities between the linear alkyl, isopropyl, cyclopropyl, and 3-oxetanyl subs...
Figure 7: Comparison of lipophilicities between isopropyl and cyclopropyl substituents grouped by exchange of...
Figure 8: Carbon extensions.
Figure 9: Experimental and theoretical (in blue) values (calculated at the MN15/aug-cc-pVTZ//MN15/cc-pVTZ lev...
Figure 10: Correlation of the DFT-calculated lipophilicities with the experimental values. A) fluorinated seri...
Figure 11: Experimental (in black) and theoretical (in blue) values (calculated at the MN15/aug-cc-pVTZ//MN15/...
Beilstein J. Org. Chem. 2017, 13, 2883–2887, doi:10.3762/bjoc.13.280
Scheme 1: The synthesis of anti-2,3-difluorobutan-1,4-diol (anti-5) [17].
Scheme 2: Improved epoxide opening and deoxofluorination conditions.
Scheme 3: Attempted synthesis of anti-5 via acetonide protection.
Scheme 4: Completion of the synthesis of anti-5.
Scheme 5: Synthesis of (±)-syn-5.
Beilstein J. Org. Chem. 2010, 6, No. 62, doi:10.3762/bjoc.6.62
Figure 1: Vicinal difluoride containing building blocks.
Scheme 1: Synthesis of meso-2,3-difluoro-1,4-butanediol.
Scheme 2: Monoprotection of 3, and activation of the remaining alcohol.
Scheme 3: Reaction of 12 leading to defluorinated products.
Figure 2: Molecular overlay of both conformers of 7.
Figure 3: Crystal packing of 7 viewed along the b axis. Short contacts (see text) are shown in light blue.
Figure 4: Crystal structure of 3.
Figure 5: Crystal packing of 3 viewed along the c axis. H-bonds are shown in light blue.