Workbook for Organic Synthesis: The Disconnection Approach (eBook)

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"

Preface vii

General References ix

1. The Disconnection Approach 1

2. Basic Principles: Synthons and Reagents: Synthesis of
Aromatic Compounds 5

3. Strategy I: The Order of Events 11

4. One-Group C-X Disconnections 15

5. Strategy II: Chemoselectivity 21

6. Two-Group C-X Disconnections 29

7. Strategy III: Reversal of Polarity, Cyclisations, Summary of
Strategy 35

8. Amine Synthesis 41

9. Strategy IV: Protecting Groups 49

10. One-Group C-C Disconnections I: Alcohols 55

11. General Strategy A: Choosing a Disconnection 61

12. Strategy V: Stereoselectivity A 67

13. One-Group C-C Disconnections II: Carbonyl Compounds
75

14. Strategy VI: Regioselectivity 81

15. Alkene Synthesis 87

16. Strategy VII: Use of Acetylenes (Alkynes) 93

17. Two-Group C-C Disconnections I: Diels-Alder Reactions
99

18. Strategy VIII: Introduction to Carbonyl Condensations
105

19. Two-Group C-C Disconnections II: 1,3-Difunctionalised
Compounds 111

20. Strategy IX: Control in Carbonyl Condensations 115

21. Two-Group C-C Disconnections III: 1,5-Difunctionalised
Compounds Conjugate (Michael) Addition and Robinson Annelation
123

22. Strategy X: Aliphatic Nitro Compounds in Synthesis 129

23. Two-Group Disconnections IV: 1,2-Difunctionalised Compounds
133

24. Strategy XI: Radical Reactions in Synthesis 139

25. Two-Group Disconnections V: 1,4-Difunctionalised Compounds
147

26. Strategy XII: Reconnection 153

27. Two-Group C-C Disconnections VI: 1,6-diCarbonyl
Compounds 159

28. General Strategy B: Strategy of Carbonyl Disconnections
165

29. Strategy XIII: Introduction to Ring Synthesis: Saturated
Heterocycles 173

30. Three-Membered Rings 181

31. Strategy XIV: Rearrangements in Synthesis 189

32. Four-Membered Rings: Photochemistry in Synthesis 195

33. Strategy XV: The Use of Ketenes in Synthesis 201

34. Five-Membered Rings 207

35. Strategy XVI: Pericyclic Reactions in Synthesis: Special
Methods for Five-Membered Rings 213

36. Six-Membered Rings 221

37. General Strategy C: Strategy of Ring Synthesis 227

38. Strategy XVII: Stereoselectivity B 235

39. Aromatic Heterocycles 245

40. General Strategy D: Advanced Strategy 255

Index 263

"The book provides an excellent and pragmatic panorama of the
various aspects of disconnective strategies, whilst keeping in mind
the importance of protective strategies." (Reviews, December
2010)