1. Literature Meeting February 20th 2006
Enantioselective Preparation of Allenes and Their Use in Organic Synthesis
By Alain Grandbois
S.K. Collins’ Group

2. Presentation Outline Introduction
Enantioselective Preparation of Allenes
Nucleophilic Attack on Alkyne
π-Allyl Complex
[3,3] Sigmatropic Rearrangement
Nucleophilic Attack of Allene Anions on Electrophiles
Total Synthesis of Natural Products
Enantioselective Synthesis With Allenes
Nucleophilic Attack of Allenyl Metals on Electrophiles
Nucleophilic Attack on Carbonyl Compounds
Photocyclisations
[3,3] Sigmatropic Rearrangements
Amination
Diels-Alder Reaction
Pauson-Khand Reaction
Nazarov Reaction
Substitution Reaction

3. Structure of an Allene

4. Allenes vs. Alkyne In Natural Products

5. Axial Chirality: How does it work?

6. Natural Products Containing Chiral Allenes

7. Presentation Outline Introduction
Enantioselective Preparation of Allenes
Nucleophilic Attack on Alkyne
π-Allyl Complex
[3,3] Sigmatropic Rearrangement
Nucleophilic Attack of the Allene Anions on Electrophiles
Total Synthesis of Natural Products
Enantioselective Synthesis With Allenes
Nucleophilic Attack of Allenyl Metals on Electrophiles
Nucleophilic Attack on Carbonyl Compounds
Photocyclisation
[3,3] Sigmatropic Rearrangements
Aminations
Diels-Alder Reaction
Pauson-Khand Reaction
Nazarov Reaction
Substitution Reaction

8. The First Enantioselective Preparation of an Allene

9. Chiral Propargylic Alcohol As Starting Material

10. Nucleophilic Attack on Alkynes

11. Nucleophilic Attack on Alkynes

12. Nucleophilic Attack on Alkynes

13. Nucleophilic Attack on Alkynes

14. Nucleophilic Attack on Alkynes

15. π-Allyl Complex

16. π-Allyl Complex

17. [3,3]-Sigmatropic Rearrangement

18. Nucleophilic Attack of Allenyl Metal on Electrophiles

19. Nucleophilic Attack of Allenyl Metal on Electrophiles

20. Proposed Mechanism

21. Wittig Reaction on Ketenes

22. Total Synthesis of Male Dried Bean Beetle Pheromone

23. Total Synthesis of (-)-Isolaurallene

24. Total Synthesis of (-)-Isolaurallene

25. Total Synthesis of (-)-Isolaurallene

27. Presentation Outline Introduction
Enantioselective Preparation of Allenes
Nucleophilic Attack on Alkyne
π-Allyl Complex
[3,3] Sigmatropic Rearrangement
Nucleophilic Attack of the Allene Anions on Electrophiles
Total Synthesis of Natural Products
Enantioselective Synthesis With Allenes
Nucleophilic Attack of Allenyl Metals on Electrophiles
Nucleophilic Attack on Carbonyl Compounds
Photocyclisations
[3,3] Sigmatropic Rearrangements
Aminations
Diels-Alder Reaction
Pauson-Khand Reaction
Nazarov Reaction
Substitution Reaction

28. Nucleophilic Attack of Allenyl Metal on Electrophiles

29. Multicomponent Coupling

30. Proposed Mechanism

31. Photocyclization

32. Lewis Acid Catalyzed [3,3]-Sigmatropic Rearrangement

33. Proposed Mechanism

34. Intramolecular Amination

35. Diels-Alder Reaction

36. Pauson-Khand Reaction

37. Nazarov Cyclization

38. Substitution

39. Proposed Mechanism

40. Central to Axial to Central: Chirality transfert Total Synthesis of (+)-Sterpurene

41. Central to Axial to Central: Chirality transfert Total Synthesis of (+)-Sterpurene

42. Central to Axial to Central: Chirality transfert Total Synthesis of (-)-Malyngolide

43. Central to Axial to Central: Chirality transfert Total Synthesis of Furanomycin

44. Central to Axial to Central: Chirality transfert Total Synthesis of Clavepictines

45. Central to Axial to Central: Chirality transfert Total Synthesis of Clavepictines (2)

46. Conclusion