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In Case You Get Bored: Propose Reasonable Mechanisms

In Case You Get Bored: Propose Reasonable Mechanisms. 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.”

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In Case You Get Bored: Propose Reasonable Mechanisms

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  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 15260

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

  19. The Rogue Homoallylic Amide

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

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