Tema 1.9 Session3

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Tema 1.9 Session3

  1. 1. Mòdul MD2301 - Formació general; 564497 – Química orgànica i inorgànica MASTER ON DRUGS, COSMETICS AND FOOD QUALITY Dr. Antonio Delgado Universitat de Barcelona October 2009
  2. 2. Session 3 Electrophilic aromatic substitution . Benzene, substituted benzenes and their reactivity with electrophiles. Directing groups. Organic synthesis . Linear versus convergent synthesis. Protecting groups in organic synthesis. Retrosynthetic analysis. Enantiopure compounds: chemical resolution of racemates.
  3. 3. Hückel’s rule : (4n+2)  electrons delocalized (conjugated) in a cyclic system Electrophilic aromatic substitution
  4. 4. Heterocyclic aromatic systems
  5. 6. Stability of aromatic systems
  6. 10. Electrophilic aromatic substitution Halogenation
  7. 11. Electrophilic aromatic substitution Nitration
  8. 12. Electrophilic aromatic substitution Sulfonation
  9. 13. Electrophilic aromatic substitution Alkylation
  10. 15. Electrophilic aromatic substitution
  11. 16. Electrophilic aromatic substitution on benzene derivatives
  12. 24. <ul><li>Construction of the carbon skeleton </li></ul><ul><li>Functional group transformations </li></ul><ul><li>Functional group protection </li></ul><ul><li>Stereochemical control (stereogenic centers) </li></ul>Planning an organic synthesis Basic steps
  13. 25. Planning an organic synthesis Construction of the carbon skeleton Linear vs convergent synthesis Linear synthesis Convergent synthesis
  14. 26. Construction of the carbon skeleton Retrosynthetic analysis: Strategic disconnections and synthon generation Reagent Real species Synthon ( “virtual”) Ionic or radical fragment arising from a disconnection
  15. 27. Equivalence between synthons and reagents
  16. 28. Functional group transformation Reduction of carbonyl derivatives
  17. 29. Functional group protection: protecting groups in peptide synthesis: Reactivity control
  18. 30. Protecting groups in peptide synthesis Directionality in peptide bond formation
  19. 31. Stereochemical control Enantiomers and chirality
  20. 32. Enantiomers can show different biological activity
  21. 33. Resolution of racemic mixtures Chiral chromatography
  22. 34. Chemical resolution (diastereomeric salt formation)
  23. 35. An example of diastereomeric salt formation
  24. 36. Resolution of racemic mixtures Diastereomeric salt formation in “high throughput format”
  25. 37. Resolution of racemic mixtures Chiral chromatography

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