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
Dr Paul Wyatt, School of Chemistry, University of
Bristol, Bristol
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.
Dr Stuart Warren, Department of Chemistry, University of
Cambridge, Lensfield Road, Cambridge
Dr Warren is the author of the bestselling textbooks Organic
Synthesis: The Disconnection Approach (Wiley) and Organic Synthesis
(OUP)
?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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