Organic Synthesis: The Disconnection Approach, 2nd Edition

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