In Case You Get Bored: Propose Reasonable Mechanisms
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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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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.”

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


Chiral Allylic Amines


Enabling Methodology: Zr→Zn Transmetalation, Aldehyde Addition

Enabling Methodology: Et2Zn Addition to Benzaldimines

Zr→Zn Transmetalation, Aldimine Addition: Optimization


Zr→Zn Transmetalation, Aldimine Addition:

Racemic Scope


Zr→Zn Transmetalation, Enantioselective Aldimine Addition


Zr→Zn Transmetalation, Aldiminium Addition


Zr→Zn Transmetalation, Diastereoselective Aldimine Addition


Mechanism Hints


Three-Component Aldimine Vinylation/Cyclopropanation:

Discovery


Three-Component Aldimine Vinylation/Cyclopropanation:

Scope


Three-Component Aldimine Vinylation/Cyclopropanation:

Relative Stereochemistry


Three-Component Aldimine Vinylation/Cyclopropanation:

Mechanism


Three-Component Aldimine Vinylation/Cyclopropanation:

Wipf Group Synthetic Applications


Tandem Zirconocene Homologation/Aldimine Allylation:

Discovery and Scope


Tandem Zirconocene Homologation/Aldimine Allylation:

Relative Stereochemistry and Mechanism


Conclusions


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


The Rogue Homoallylic Amide


Transition-Metal-Mediated Cascade Reactions: C,C-Dicyclopropylmethylamines

By Way of Double C,C-s-Bond Insertion into Bicyclobutanes


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