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Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40
Graphical Abstract
Figure 1: Some important bioactive molecules with an azide group.
Scheme 1: Epoxidation of azido nitrobenzoate 8.
Scheme 2: Methanolysis of the mixture of isomeric epoxides 9a and 9b.
Figure 2: The X-ray crystal structure of 10.
Scheme 3: Suggested mechanism for the reaction of the isomeric epoxides 9a and 9b with HCl(g) in MeOH.
Figure 3: Relative free energy profile for the methanolysis of the isomeric epoxides 9.
Figure 4: Mulliken charge analysis of protonated epoxide intermediates 12 and 15.
Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7
Figure 1: Examples of natural products containing β-amino acids.
Scheme 1: Synthesis of cyclic β-amino acid 6.
Scheme 2: Epoxidation of Boc-protected amino ester 4 and hydrolysis of epoxide 7 with HCl(g)–MeOH.
Scheme 3: Reaction of epoxide 7 with NaHSO4 in methylene chloride/MeOH.
Scheme 4: Synthesis of cyclic β-amino acid derivative 8.
Scheme 5: Suggested mechanism for the reaction of epoxide 7 with NaHSO4.
Figure 3: Solvent-corrected relative free energy profile at 298.15 K for the reaction mechanism of 14 shown i...
Figure 4: Solvent-corrected relative free energy profile at 298.15 K for the reaction mechanism of 17 shown i...
Figure 5: The optimized geometries of the conformers 7a and 7b with selected interatomic distances at the B3L...