Table of Contents

Preface ix

General References xi

1. The Disconnection Approach 1

2. Basic Principles: Synthons and Reagents Synthesis of Aromatic Compounds 7

3. Strategy I: The Order of Events 17

4. One-Group C–X Disconnections 23

5. Strategy II: Chemoselectivity 29

6. Two-Group C–X Disconnections 35

7. Strategy III: Reversal of Polarity, Cyclisations, Summary of Strategy 45

8. Amine Synthesis 53

9. Strategy IV: Protecting Groups 61

10. One Group C–C Disconnections I: Alcohols 69

11. General Strategy A: Choosing a Disconnection 77

12. Strategy V: Stereoselectivity A 83

13. One Group C–C Disconnections II: Carbonyl Compounds 93

14. Strategy VI: Regioselectivity 101

15. Alkene Synthesis 107

16. Strategy VII: Use of Acetylenes (Alkynes) 115

17. Two-Group C–C Disconnections I: Diels-Alder Reactions 121

18. Strategy VIII: Introduction to Carbonyl Condensations 129

19. Two-Group C–C Disconnections II: 1,3-Difunctionalised Compounds 133

20. Strategy IX: Control in Carbonyl Condensations 139

21. Two-Group C–C Disconnections III: 1,5-Difunctionalised Compounds Conjugate (Michael) Addition and Robinson Annelation 151

22. Strategy X: Aliphatic Nitro Compounds in Synthesis 161

23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds 167

24. Strategy XI: Radical Reactions in Synthesis 177

25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds 185

26. Strategy XII: Reconnection 193

27. Two-Group C–C Disconnections VI: 1,6-diCarbonyl Compounds 199

28. General Strategy B: Strategy of Carbonyl Disconnections 207

29. Strategy XIII: Introduction to Ring Synthesis: Saturated Heterocycles 217

30. Three-Membered Rings 229

31. Strategy XIV: Rearrangements in Synthesis 237

32. Four-Membered Rings: Photochemistry in Synthesis 245

33. Strategy XV: The Use of Ketenes in Synthesis 251

34. Five-Membered Rings 255

35. Strategy XVI: Pericyclic Reactions in Synthesis: Special Methods for Five-Membered Rings 261

36. Six-Membered Rings 269

37. General Strategy C: Strategy of Ring Synthesis 279

38. Strategy XVII: Stereoselectivity B 289

39. Aromatic Heterocycles 301

40. General Strategy D: Advanced Strategy 313

Index 325

About the Author

Dr Stuart Warren, Department of Chemistry, University of Cambridge, UK
Dr Warren is the author of the bestselling textbooks Organic Synthesis: The Disconnection Approach (Wiley), Organic Synthesis: Strategy and Control (Wiley) and Organic Chemistry (OUP).

Dr Paul Wyatt, School of Chemistry, University of Bristol, UK
Dr Wyatt is Director of Undergraduate Studies for the School of Chemistry at Bristol University and also Director of BRISTOL ChemLabS - a HEFCE Centre for Excellence in Teaching & Learning. He is co-author, with Warren, of Organic Synthesis: Strategy and Control.

Reviews

The authors have succeeded admirably in the updating of a classic in the pedagogy of organic chemistry. ( Journal of Medicinal Chemistry , August 2009) This book is suitable for advanced undergraduate students, researchers and professional chemists. Both the writing and the diagrams are simple and clear. ( Reviews, May 2009)