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Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123
Graphical Abstract
Figure 1: Classification of AMYs.
Scheme 1: Aminoester- and amino acid-based AMYs for single and double [3+2] cycloadditions.
Scheme 2: Formation of semi-stabilized AMYs B1 from pyrrolidines.
Scheme 3: Cyclic amine-based AMYs A3 and B1 for [3 + 2] cycloadditions.
Scheme 4: Proposed double cycloaddition reactions involving semi-stabilized AMYs.
Scheme 5: [3 + 2] Cycloaddition for the synthesis of trifluoromethylated pyrrolidines 9.
Figure 2: Biologically interesting pyrrolizidines.
Scheme 6: Double cycloadditions with glycine for the synthesis of products 10 (dr > 9:1).
Scheme 7: Double cycloadditions with α-substituted amino acids leading to products 11 (≈8.5:1 dr).
Scheme 8: Stereochemistry for the formation of products 10 or 11.
Scheme 9: One-pot and stepwise double cycloadditions. Conditions: i) MeCN (0.02 M), 90 °C, 6 h; ii) then AcOH...
Figure 3: Biologically interesting spirooxindole-pyrrolizidines.
Scheme 10: Double cycloadditions for the synthesis of bis[spirooxindole-pyrrolizidine]s.
Scheme 11: Mechanism for the diastereoselective synthesis of bis[spirooxindole-pyrrolizidine]s.
Scheme 12: Stepwise synthesis of triazolobenzodiazepine 21a.
Scheme 13: One-pot synthesis of triazolobenzodiazepines.
Figure 4: Bioactive triazolobenzodiazepine derivatives.
Scheme 14: One-pot synthesis of tetrahydropyrroloquinazolines.
Scheme 15: One-pot synthesis of tetrahydropyrrolobenzodiazepines.
Figure 5: Bioactive pyrroloquinazolines and pyrrolobenzodiazepines.
Scheme 16: Stepwise synthesis of pyrrolo[2,1-a]isoquinolines.
Figure 6: Bioactive pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines.
Figure 7: Bioactive tetrahydropyrrolothiazoles.
Scheme 17: Pseudo-four-component reaction for the synthesis of tetrahydropyrrolothiazoles 29 and 30 (>4:1 dr).
Scheme 18: One-pot two-step synthesis of spirooxindole-pyrrolothiazoles 31 (>4:1 dr).
Beilstein J. Org. Chem. 2020, 16, 1225–1233, doi:10.3762/bjoc.16.106
Figure 1: Bioactive pyrrolo[2,1-a]isoquinolines and hexahydropyrrolo[2,1-a]isoquinolines.
Scheme 1: [3 + 2] Cycloaddition with amino esters or amino acids.
Scheme 2: Scaffolds derived from the initial [3 + 2] adducts.
Scheme 3: [3 + 2] Cycloaddition with amino esters or amino acids. Conditions: 1:3:4 (1.2:1:1.1), Et3N (1.5 eq...
Scheme 4: Synthesis of pyrrolo[2,1-a]isoquinolines 9. Reaction conditions: 5 (0.5 mmol, 1 equiv), 7 (3 equiv)...
Scheme 5: Synthesis of pyrrolo[2,1-a]isoquinolines 11. Reaction conditions: 6 (0.5 mmol, 1 equiv), 7 (3 equiv...
Scheme 6: Synthesis of pyrrolo[2,1-a]isoquinolines 12. Reaction conditions: 5 or 6 (0.5 mmol, 1 equiv), cinna...
Scheme 7: Plausible mechanism for the synthesis of 9a.