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Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148
Graphical Abstract
Scheme 1: Oxazolidinone (1), five-membered cyclic carbonate (2) and some important compounds containing an ox...
Scheme 2: Proposed mechanisms by Keshava Murthy and Dhar [41] and De Meijere and co-workers [42].
Figure 1: Possible pathways for the formation of oxazolidinone intermediates 10 and 11. Optimized transition ...
Figure 2: Potential energy profile related to the formation of oxazolidinone intermediates 10 and 11 at the P...
Figure 3: IRC calculated for the formation of (a) 10 and (b) 11 at M06-2X/6-31+G(d,p) level. I-1, I-15, I-35, ...
Figure 4: Optimized geometries for the stationary points for the formation of 10 at PCM(DCM)/M06-2X/6-31+G(d,...
Scheme 3: Proposed mechanisms for the formation of oxazolidinone 9f.
Figure 5: Potential energy profiles for paths 1a (blue), 1b (red), 2 (green) and relative Gibbs free energies...
Figure 6: Optimized geometries for the stationary points of path 1b at PCM(DCM)/M06-2X/6-31+G(d,p)//M06-2X/6-...
Scheme 4: Proposed mechanism for the formation of five-membered cyclic carbonate 8f.
Figure 7: Potential energy profile and relative Gibbs free energies (kcal/mol) in DCM related to the formatio...
Figure 8: Optimized geometries for the stationary points of step 1 for the formation of 16 at PCM(DCM)/M06-2X...
Figure 9: Optimized geometries for the stationary points of step 2 for the formation of 17 at PCM(DCM)/M06-2X...
Figure 10: Optimized geometries for the stationary points of step 3 for the formation of PC8 at PCM(DCM)/M06-2...
Beilstein J. Org. Chem. 2010, 6, No. 15, doi:10.3762/bjoc.6.15
Scheme 1: Synthesis of bis-carbamate 12 and oxazolidinone 13.
Scheme 2: Mechanism of the palladium-catalyzed ionization/cyclization reaction.
Scheme 3: Synthesis of aminocyclitol analogue 6.
Figure 1: The thermal ellipsoid plot of the single crystal X-ray crystallographic structure of 18.
Scheme 4: Synthesis of oxazolidone 23.
Scheme 5: Mechanism of the palladium-catalyzed ionization/cyclization reaction in dichloro biscarbamate 22.
Scheme 6: Synthesis of dichloroaminocyclitol 7.
Figure 2: 1H NMR NOE spectrum of compound 7.