Wacker Oxidation and Wacker-Type Reactions

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Presentation transcript:

Wacker Oxidation and Wacker-Type Reactions /52

The Wacker Process

Overview on Wacker Oxidation

Mechanism of the Wacker Oxidation: High Cl- Concentration

Mechanism of the Wacker Oxidation: Low Cl- Concentration

By-Products Observed in the Wacker Oxidation: Isomerization of Alkenes

By-Products in the Wacker Oxidation: Chlorination Products

By-Products in the Wacker Oxidation: Allylic Oxidation Products

By-Products in the Wacker Oxidation: Oxidative Cleavage Products

Variation to the Classical Wacker Oxidation: Co-Oxidant

Variation to the Classical Wacker Oxidation: Co-Oxidant

Variation to the Classical Wacker Oxidation: Solid Phase Supported Catalyst

Variation to the Classical Wacker Oxidation: Phase Transfert Catalyst

Variation to the Classical Wacker Oxidation: Biphasic System

Chemoselectivity of Wacker Oxidation: Steric Hindrance

Chemoselectivity of Wacker Oxidation: External vs Internal Alkenes

Chemoselectivity of Wacker Oxidation: Steric Hindrance

Chemoselectivity of Wacker Oxidation: Compatibility with Functional Groups

Chemoselectivity of Wacker Oxidation: Compatibility with Functional Groups

Wacker-Type External Oxo-Nucleophiles Addition

Wacker-Type Amino Cyclisation (Oxidative Amination)

Wacker-Type Amino Cyclisation (Oxidative Amination)

Proposed Catalytic Cycle for Copper Free Wacker-Type Reaction

Wacker-Type External Amino-Nucleophile Addition

Asymmetric Wacker-Type Cyclization

Asymmetric Wacker-Type Cyclization

Catalytic Asymmetric Wacker-Type Cyclization: Limited to Tetrasubstituted Alkenes

Catalytic Asymmetric Wacker-Type Cyclization: Limited to Trisubstituted Alkenes

Catalytic Asymmetric Wacker-Type Cyclization: 6-Membereds Rings

Stereochemistry of the Oxypalladation Step

Stereochemistry of the Oxypalladation Step

Stereochemistry of the Oxypalladation Step

Stereochemistry of the Oxypalladation Step

Desymmetrization by Wacker-Type Cyclization

Desymmetrization by Wacker-Type Cyclization

Anti-Markovnikov Wacker Oxidation

Anti-Markovnikov Products: Steric Effect

Anti-Markovnikov Products: Proximal Complexing Function

Anti-Markonikov Products: Proximal Complexing Function

Anti-Markovnikov Products: Proximal Complexing Function

Anti-Markovnikov Products: Proximal Double Bond

Anti-Markovnikov Oxidative Amination

Anti-Markovnikov Products: Cationic Rhodium Complex

Formation of Allylic Acetates under Wacker Oxidation Conditions

Formation of Allylic Acetates in Wacker Conditions: Effect of Solvent

Formation of Branched Allylic Acetates

Formation of Branched Allylic Acetates

Formation of Linear Allylic Acetates

Application to the Total Synthesis of Garsubellin A

Application to the Total Synthesis of Calyculin A and B

Application to Total Synthesis

Conclusion

Anti-Markovnikov Products: Cationic Rhodium Complex

Anti-Markonikov Products: Proximal Complexing Function

To the Frontier of Wacker-Type Reactions: Wacker-Type Heteroannulation Process

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