1. In Case You Get Bored: Propose Reasonable Mechanisms

2. Hydrozirconation/Zr→Zn Transmetalation/Aldimine Addition:
One-pot Synthesis of Allylic, C-Cyclopropyl
and Homoallylic Amines from Alkynes.
“The time is apt for synthetic chemists to fully enter the world of organozirconium … chemistry.”
V. Snieckus in Titanium and Zirconium in Organic Synthesis, I. Marek, Ed., Wiley-VCH, Germany, 2002.
Christopher Kendall and Prof. Peter Wipf
Dept. of Chemistry, University of Pittsburgh
Pittsburgh, PA

3. Chiral Allylic Amines

4. Enabling Methodology: Zr→Zn Transmetalation, Aldehyde Addition
Enabling Methodology: Et2Zn Addition to Benzaldimines
Zr→Zn Transmetalation, Aldimine Addition: Optimization

5. Zr→Zn Transmetalation, Aldimine Addition:
Racemic Scope

6. Zr→Zn Transmetalation, Enantioselective Aldimine Addition

7. Zr→Zn Transmetalation, Aldiminium Addition

8. Zr→Zn Transmetalation, Diastereoselective Aldimine Addition

9. Mechanism Hints

10. Three-Component Aldimine Vinylation/Cyclopropanation:
Discovery

11. Three-Component Aldimine Vinylation/Cyclopropanation:
Scope

12. Three-Component Aldimine Vinylation/Cyclopropanation:
Relative Stereochemistry

13. Three-Component Aldimine Vinylation/Cyclopropanation:
Mechanism

14. Three-Component Aldimine Vinylation/Cyclopropanation:
Wipf Group Synthetic Applications

15. Tandem Zirconocene Homologation/Aldimine Allylation:
Discovery and Scope

16. Tandem Zirconocene Homologation/Aldimine Allylation:
Relative Stereochemistry and Mechanism

17. Conclusions

18. Aventis Pharmaceuticals Dr. Steve Geib: X-rays Dr. Fu Tyan Lin: 2H NMR
Acknowledgements
Prof. Peter Wipf
Prof. Dennis Curran
Prof. Scott Nelson
Prof. Billy Day
Prof. Paul Floreancig
NSF
Aventis Pharmaceuticals
Dr. Steve Geib: X-rays
Dr. Fu Tyan Lin: 2H NMR
Wipf Group Members Past and Present
2004
2002

19. The Rogue Homoallylic Amide

20. By Way of Double C,C-s-Bond Insertion into Bicyclobutanes
Transition-Metal-Mediated Cascade Reactions: C,C-Dicyclopropylmethylamines
By Way of Double C,C-s-Bond Insertion into Bicyclobutanes