In Case You Get Bored: Propose Reasonable Mechanisms

Slides:

Advertisements

Similar presentations

Literature Meeting March 25, 2008 Buchwald-Hartwig Coupling : Discovery, Optimization, and Applications David Marcoux Charette’s Laboratories.

Advertisements

Created by Athena Anderson, Brette Chapin, Michelle Hansen and Kanny Wan and posted on VIPEr June Copyright Brette Chapin This work is licensed.

Center for Catalysis Research and Innovation

Continuous Catalytic Oxidation in Pharmaceutical Processing B. Frank Gupton VCU John Monnier USC Steve Fong VCU Center for Rational Catalyst Synthesis.

1 CH402 Asymmetric catalytic reactions Prof M. Wills Think about chiral centres. How would you make these products? Think about how you would make them.

Recent Development for Stereoselective Synthesis of 1,3-Polyol Ye Zhu Prof. Burgess’ Group Aug. 19, 2010.

Lecture 14 APPLICATIONS IN ORGANIC SYNTHESIS Copyright ©The McGraw-Hill Companies, Inc. Permission required for reproduction or display.

Faculty of Allied Medical Sciences

Organic Chemistry William H. Brown & Christopher S. Foote.

1 Literature Screening JACS Synthesis February 2 nd 2009 Thibaud Gerfaud.

1 CATALYTIC ASYMMETRIC NOZAKI- HIYAMA-KISHI REACTION: ROLE OF ORGANOCHROMIUM COMPOUNDS AND NOVEL SALEN LIGANDS A RKAJYOTI C HAKRABARTY Prof. Uday Maitra’s.

Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins Via an Ene Reaction / [2,3]-Rearrangement Hongli Bao & Uttam K. Tambar Guillaume.

Advances in Metal Mediated Intramolecular Enyne Carbocyclizations Patrick D. Pohlhaus The University of North Carolina at Chapel Hill March 28, 2003.

1 Year 3 CH3E4 notes: Asymmetric Catalysis, Prof Martin Wills Reorganised to highlight key areas to learn and understand. You are aware of the importance.

High-Oxidation-State Palladium Catalysis 报告人：刘槟 2010 年 10 月 23 日.

1 Year 3 CH3E4 notes: Asymmetric Catalysis, Prof Martin Wills You are aware of the importance of chirality. This course will focus on asymmetric.

CHEM 2411 Review What did you learn in Organic Chemistry I?

Ye Zhu 09/02/10 Burgess’s Group Meeting Chiral Ligands On A Spiro Scaffold for Transition-Metal- Catalyzed Asymmetric Reactions Work by Prof. Zhou Qi-Lin.

1 Applications of a Novel Nickel-Catalyzed Reductive Coupling Reaction Towards the Total Synthesis of Amphidinolide T1 Julie Farand April 1 st, 2004 Jamison.

Supervisor: Yong Huang Reporter: Qian Wang Date: Magical Chiral Spirobiindane Skeletons.

Atom-Economical and Sustainable C-N Bond Formation Reactions from Alcohols and N-Sources via Catalytic Hydrogen Transfer Reactions September 15th, 2015.

Rhodium-Catalyzed Chemo- and Regioselective Decarboxylative Addition of β- Ketoacids to Allenes: Efficient Construction of Tertiary and Quaternary Carbons.

ORGANIC SYNTHESIS CONTENTS Introduction Functional groups

Wacker Oxidation and Wacker-Type Reactions

Jean-Louis Brochu Department of Chemistry University of Ottawa

Indium in Organic Synthesis Huang-Jianzhou

1 Orlando, September 2015 Atom and Step Economy in Synthetic Organic Chemistry Department of Organic Chemistry, University of Alicante, Alicante, Spain.

9.7 Catalytic Hydrogenation The addition of H 2 across a C=C double bond If a chirality center is formed, syn addition is observed Draw the stereoisomers.

24-1 Diels-Alder Reaction  Diels-Alder reaction:  Diels-Alder reaction: A cycloaddition reaction of a conjugated diene and certain types of double and.

Enantioselective Reactions Catalyzed by Iron Complexes Pablo Pérez.

Singlet oxygen: From discovery to natural and biologically active product synthesis November, th 2005 By Isabelle Bonnaventure Literature Meeting.

8 Rearrangements of Carbanions and Free Radicals.

Synthetic Division Examples

Organic Chemistry Second Edition Chapter 11 David Klein

Dr. Christopher Cioffi Monday 3/20/2017 9:00AM – 9:50AM

9.5 Oxymercuration-Demercuration

Area of the Interest Development of new organocatalytic methodologies

Major developments in Rh-catalyzed asymmetric 1,4-addition of boron species to enone Group Seminar By Raphaël Beltran.

Efficiency in Synthesis

Klein, Organic Chemistry 1e

Why study Organic Synthesis?

Transition Metal Catalyzed Amide Bond Formation

Guillaume Benoit – Charette Group

Aromatization using gold catalysis

学堂讲座通知化学系 Prof. Liming Zhang 加州大学Santa Barbara分校

Development of Catalytic Reactions using Well-Defined Monomeric Cu(I)

Organometallic Compounds

Building Enantioselective Ligands: New Frontiers with Oxazolines

Mike April 29th 2013 Umpolung of Hemiaminals: Titanocene-Catalyzed Dehydroxylative Radical Coupling Reactions with Activated Alkenes Zheng, X.; Dai, X.-J.;

C-H Insertion on sulfonyl compounds Synthesis of Plakortethers

Literature Meeting February 20th 2006

Enantioselective Nucleophilic Catalysis for the Synthesis of β-Lactams and other Nitrogen Containing Heterocycles from Isocyanates James A. MacKay, Department.

Copper Hydride Catalyzed Hydroamination of Alkenes and Alkynes

Adam R. Johnson Department of Chemistry

Abigail G. Doyle, Department of Chemistry, Princeton University

YLIDES Dr. A. G. Nikalje.

B-Hydroxysalicylhydrazones: Chiral, non-racemic tridentate catalysts for asymmetric synthesis Shawn R. Hitchcock, Department of Chemistry, Illinois State.

Organ metallic Compounds

Bonds to 10 and 100 Hint: Use your bonds to 10 to work out bonds to – 5 =  10 – 8 =  10 – 3 =  10 – 10 =  100 – 30 =  40 +  = – 90.

Synthesis and Reactions of Methyleneaziridines

Shawn R. Hitchcock, Department of Chemistry, Illinois State University

Enantioselective Nucleophilic Catalysis for the Synthesis of β-Lactams and other Nitrogen Containing Heterocycles from Isocyanates James A. MacKay, Department.

Development of Chiral Lewis Base as Novel Nucleophilic Catalysts and Their Application in Asymmetric Synthesis Xiaodong Michael Shi, Department of Chemistry,

Hydrohalogenation Section 9.3.

John D. Chisholm, Syracuse University, Syracuse, NY 13244

John D. Chisholm, Syracuse University, Syracuse, NY 13244

Chapter 11 Amines Adel M. Awadallah Islamic University of Gaza

Catalytic Enantio- and Diastereoselective Allylations with Nucleophilic p-Allylpalladium Complexes Elizabeth R. Jarvo, Department of Chemistry, University.

CONTENTS  INTRODUCTION  REACTION  MECHANISM  APPLICATION  SCOPE  CONCLUSION  REFERENCE.

CONTENTS  INTRODUCTION  REACTION  MECHANISM  APPLICATION  SCOPE  CONCLUSION  REFERENCE.

Presentation transcript:

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

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

The Rogue Homoallylic Amide

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