In Case You Get Bored: Propose Reasonable Mechanisms
This presentation is the property of its rightful owner.
Sponsored Links
1 / 20

In Case You Get Bored: Propose Reasonable Mechanisms PowerPoint PPT Presentation


  • 60 Views
  • Uploaded on
  • Presentation posted in: General

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.”

Download Presentation

In Case You Get Bored: Propose Reasonable Mechanisms

An Image/Link below is provided (as is) to download presentation

Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author.While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server.


- - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - -

Presentation Transcript


In case you get bored propose reasonable mechanisms

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.”

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


In case you get bored propose reasonable mechanisms

Chiral Allylic Amines


In case you get bored propose reasonable mechanisms

Enabling Methodology: Zr→Zn Transmetalation, Aldehyde Addition

Enabling Methodology: Et2Zn Addition to Benzaldimines

Zr→Zn Transmetalation, Aldimine Addition: Optimization


In case you get bored propose reasonable mechanisms

Zr→Zn Transmetalation, Aldimine Addition:

Racemic Scope


In case you get bored propose reasonable mechanisms

Zr→Zn Transmetalation, Enantioselective Aldimine Addition


In case you get bored propose reasonable mechanisms

Zr→Zn Transmetalation, Aldiminium Addition


In case you get bored propose reasonable mechanisms

Zr→Zn Transmetalation, Diastereoselective Aldimine Addition


In case you get bored propose reasonable mechanisms

Mechanism Hints


In case you get bored propose reasonable mechanisms

Three-Component Aldimine Vinylation/Cyclopropanation:

Discovery


In case you get bored propose reasonable mechanisms

Three-Component Aldimine Vinylation/Cyclopropanation:

Scope


In case you get bored propose reasonable mechanisms

Three-Component Aldimine Vinylation/Cyclopropanation:

Relative Stereochemistry


In case you get bored propose reasonable mechanisms

Three-Component Aldimine Vinylation/Cyclopropanation:

Mechanism


In case you get bored propose reasonable mechanisms

Three-Component Aldimine Vinylation/Cyclopropanation:

Wipf Group Synthetic Applications


In case you get bored propose reasonable mechanisms

Tandem Zirconocene Homologation/Aldimine Allylation:

Discovery and Scope


In case you get bored propose reasonable mechanisms

Tandem Zirconocene Homologation/Aldimine Allylation:

Relative Stereochemistry and Mechanism


In case you get bored propose reasonable mechanisms

Conclusions


In case you get bored propose reasonable mechanisms

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


In case you get bored propose reasonable mechanisms

The Rogue Homoallylic Amide


In case you get bored propose reasonable mechanisms

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

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


  • Login