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Workbook for Organic Synthesis: Strategy and Control

Workbook for Organic Synthesis: Strategy and Control

Paul Wyatt, Stuart Warren

ISBN: 978-0-471-92964-2 July 2008 502 Pages


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  • This workbook accompanies Organic Synthesis: Strategy and Control, the bestselling advanced organic textbook
  • Provides a complete course for advanced organic students and includes a graded set of problems, solutions and discussions to illustrate and develop the themes of each of the chapters in the textbook

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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. σ-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

?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)
  • Provides a comprehensive graded set of problems to illustrate and develop the themes in the textbook:  Organic Synthesis: Strategy and Control (ISBN 9780471929635)
  • Each problem is followed by a fully explained solution and discussion
  • Takes a mechanistic approach, which explains reactions and gives guidelines on how reactions might behave in different situations
  • Focuses on reactions that really work rather than those with limited application
  • By working through these examples students will develop their skills in analyzing synthetic challenges, and build a toolkit of strategies for planning new syntheses.
  • Organized using the same structure as the textbook