Free download Organic Synthesis Strategy and Control By Paul Wyatt and Stuart Warren

Authors of:  Organic Synthesis Strategy and Control By Paul Wyatt and Stuart Warren

Paul Wyatt

Stuart Warren

Table of Contents in Organic Structures from Spectra By L. D. Field 4th Edition

Preface  

A: Introduction: Selectivity

Planning Organic Syntheses: Tactics, Strategy and Control  

Chemoselectivity  

Regioselectivity: Controlled Aldol Reactions  

Stereoselectivity: Stereoselective Aldol Reactions  

Alternative Strategies for Enone Synthesis  

Choosing a Strategy: The Synthesis of Cyclopentenones  

B: Making Carbon–Carbon Bonds

The Ortho Strategy for Aromatic Compounds  

σ-Complexes of Metals  

Controlling the Michael Reaction  

Specifi c Enol Equivalents  

Extended Enolates  

Allyl Anions  

Homoenolates  

Acyl Anion Equivalents  

C: Carbon–Carbon Double Bonds

Synthesis of Double Bonds of Defi ned Stereochemistry  

Stereo-Controlled Vinyl Anion Equivalents  

Electrophilic Attack on Alkenes  

Vinyl Cations: Palladium-Catalysed C–C Coupling  

Allyl Alcohols: Allyl Cation Equivalents (and More)  

D: Stereochemistry

Control of Stereochemistry – Introduction  

Controlling Relative Stereochemistry  

Resolution  

The Chiral Pool — Asymmetric Synthesis with Natural Products as

Starting Materials —  

Asymmetric Induction I Reagent-Based Strategy  

Asymmetric Induction II Asymmetric Catalysis: Formation of C–O

and C–N Bonds  

Asymmetric Induction III Asymmetric Catalysis: Formation of C–H

and C–C Bonds  

Asymmetric Induction IV Substrate-Based Strategy  

Kinetic Resolution  

Enzymes: Biological Methods in Asymmetric Synthesis  

New Chiral Centres from Old — Enantiomerically Pure

Compounds & Sophisticated Syntheses —  

Strategy of Asymmetric Synthesis  

E: Functional Group Strategy

Functionalisation of Pyridine  

Oxidation of Aromatic Compounds, Enols and Enolates  

Functionality and Pericyclic Reactions: Nitrogen Heterocycles by

Cycloadditions and Sigmatropic Rearrangements  

Synthesis and Chemistry of Azoles and other Heterocycles with Two

or more Heteroatoms  

Tandem Organic Reactions  

General References  

Index  

The book opens with a preface, setting the stage for exploring the principles and tactics of organic synthesis. Part A begins with an introduction to the concept of selectivity, emphasizing the careful planning required for organic syntheses.

This section covers various types of selectivity crucial in synthesis, such as chemoselectivity, which involves choosing reactions that distinguish between different functional groups, and regioselectivity, which focuses on reactions like controlled aldol reactions to determine where bonds form within a molecule.

Stereoselectivity is also highlighted, discussing how to control stereochemistry in aldol reactions. Additionally, alternative strategies for synthesizing enones are explored, culminating in the example of cyclopentenone synthesis, which serves as a case study on selecting the appropriate synthesis strategy.

Part B discusses strategies for making carbon–carbon bonds, particularly in aromatic compounds through the ortho strategy, which involves directing substituents to specific positions around an aromatic ring. It delves into the role of sigma complexes with metals and ways to control the Michael reaction to produce desired products.

The use of specific enol equivalents and extended enolates is examined to show how these intermediates contribute to carbon–carbon bond formation. Other methods for creating carbon–carbon bonds are explained, including allyl anions, homoenolates, and acyl anion equivalents, which provide chemists with versatile tools for constructing complex molecules.

Part C focuses on the synthesis of carbon–carbon double bonds with defined stereochemistry. Techniques are presented for achieving stereo-controlled vinyl anion equivalents and controlling electrophilic attacks on alkenes. A significant portion of this section examines the formation of vinyl cations, highlighting the role of palladium-catalyzed C–C coupling reactions as a powerful method in organic synthesis. The chemistry of allyl alcohols is discussed, covering how allyl cation equivalents and related species can be manipulated to create double bonds and introduce complexity into molecular structures.

Part D centers on stereochemistry and introduces methods for controlling the relative stereochemistry of molecules. Resolution techniques are explained, along with the use of the “chiral pool,” which refers to the use of chiral natural products as starting materials to achieve asymmetric synthesis. The section goes into detail on asymmetric induction strategies, exploring reagent-based strategies and asymmetric catalysis for forming bonds such as C–O, C–N, C–H, and C–C.

These discussions cover both substrate-based strategies for asymmetric induction and the concept of kinetic resolution. Additionally, biological methods in asymmetric synthesis are explored, with enzymes highlighted for their role in creating chiral centers. The section wraps up by exploring enantiomerically pure compounds and complex syntheses that introduce new chiral centers in molecules.

Part E focuses on the functional group strategy in organic synthesis, beginning with methods for functionalizing pyridine. It continues with the oxidation of aromatic compounds, enols, and enolates, which are essential for modifying the functional groups within molecules.

This part also looks at the interplay between functionality and pericyclic reactions, including cycloadditions and sigmatropic rearrangements, which are especially useful in synthesizing nitrogen heterocycles. The synthesis and chemistry of azoles and other nitrogen-containing heterocycles with multiple heteroatoms are examined, showing how these compounds can be constructed with controlled properties.

The final topics in Part E include tandem organic reactions, which allow for multiple transformations in a single sequence, streamlining the synthesis process. The book provides a range of references for further reading and includes a comprehensive index to assist readers in navigating the diverse topics covered in each section.

This combination of strategic planning, selectivity control, carbon–carbon and carbon–carbon double-bond formation, stereochemistry, and functional group transformations offers a broad and in-depth approach to organic synthesis, allowing readers to develop a well-rounded understanding of the subject.

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