Workbook for Organic Synthesis. Strategy and Control

  • ID: 2251951
  • Book
  • 500 Pages
  • John Wiley and Sons Ltd
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Workbook for Organic Synthesis: Strategy and Control

Paul WyattReader and Director of Undergraduate Studies, School of Chemistry, University of Bristol, UK

Stuart WarrenReader in Organic Chemistry, Department of Chemistry, University of Cambridge, UK.

Workbook for Organic Synthesis: Strategy and Control

This workbook provides a comprehensive graded set of problems to illustrate and develop the themes of each of the chapters in the textbook Organic Synthesis: Strategy and Control. Each problem is followed by a fully explained solution and discussion. The examples extend the student s experience of the types of molecules being synthesised by organic chemists, and the strategies they employ to control their syntheses. By working through these examples students will develop their skills in analysing synthetic challenges, and build a toolkit of strategies for planning new syntheses. Together the workbook and textbook provide a complete course in advanced organic synthesis.

Organic Synthesis: Strategy and Control

Organic Synthesis: Strategy and Control is a sequel to Stuart Warren s bestseller Organic Synthesis: The Disconnection Approach. The Disconnection book concentrated on the planning behind the synthesis of compounds. This book focuses on putting the planning into practice. The two themes of the book are strategy and control: solving problems either by finding an alternative strategy or by controlling any established strategy to make it work.

The book is divided into five sections that deal with selectivity, carbon–carbon single bonds, carbon–carbon double bonds, stereochemistry and functional group strategy. Interpenetrating this structure, the 36 chapters start with classic methods and progress to modern methods and modern strategic considerations. Heterocyclic chemistry is treated throughout the book with full mechanistic explanations as part of organic chemistry rather than a separate entity.

Students and professional chemists familiar with Organic Synthesis: The Disconnection Approach will enjoy the leap into a book designed for chemists at the coalface of organic synthesis.

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Preface vii

A: Introduction: Selectivity 1

1. Planning Organic Syntheses: Tactics, Strategy and Control 3

2. Chemoselectivity 7

3. Regioselectivity: Controlled Aldol Reactions 19

4. Stereoselectivity: Stereoselective Aldol Reactions 35

5. Alternative Strategies for Enone Synthesis 47

6. Choosing a Strategy: The Synthesis of Cyclopentenones 57

B: Making Carbon Carbon Bonds 69

7. The Ortho Strategy for Aromatic Compounds 71

8. –Complexes of Metals 91

9. Controlling the Michael Reaction 103

10. Specific Enol Equivalents 115

11. Extended Enolates 123

12. Allyl Anions 135

13. Homoenolates 147

14. Acyl Anion Equivalents 155

C: Carbon Carbon Double Bonds 169

15. Synthesis of Double Bonds of Defined Stereochemistry 171

16. Vinyl Anions 191

17. Electrophilic Attack on Alkenes 203

18. Vinyl Cations 221

19. Allyl Alcohols: Allyl Cation Equivalents (and More) 241

D: Stereochemistry 257

20. Control of Stereochemistry Introduction 259

21. Diastereoselectivity 269

22. Resolution 283

23. The Chiral Pool: Asymmetric Synthesis with Natural Products as Starting Materials 295

24. Asymmetric Induction I: Reagent–Based Strategy 309

25. Asymmetric Induction II: Asymmetric Catalysis: Formation of C O and C N Bonds 321

26. Asymmetric Induction III: Asymmetric Catalysis: Formation of C H and C C Bonds 335

27. Asymmetric Induction IV: Substrate–Based Strategy 351

28. Kinetic Resolution 365

29. Enzymes: Biological Methods in Asymmetric Synthesis 377

30. New Chiral Centres from Old: Enantiomerically Pure Compounds and Sophisticated Syntheses 391

31. Strategy of Asymmetric Synthesis 405

E: Functional Group Strategy 417

32. Functionalisation of Pyridine 419

33. Oxidation of Aromatic Rings and of Enol(ate)s 433

34. Functionality and Pericyclic Reactions: Nitrogen Heterocycles by Cycloadditions and Sigmatropic Rearrangements 447

35. Synthesis and Chemistry of Azoles and other Heterocycles with Two or more Heteroatoms 459

36. Tandem Organic Reactions 473

Index 483

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?This is a must–read for any final year undergrad or PhD? student in organic chemistry, but it′s more than that?it′s a book for experienced chemists too.? (Reviews, May 2009)
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