Level 1 1
Case 1. A Surprise in the Synthesis of Guanacastepene A 1
Case 2. Sulfenylation of Indole 7
Case 3. Substrate Selective Reactions in the Presence of Lewis Acids 13
Case 4. Diastereoselective Reductions of β-Ketoesters 21
Case 5. Rearrangements from Tetrahydropyran Derivatives 27
Case 6. Stereospecific Substitution Reactions of Epoxy Sulfides 33
Case 7. NaBH4 Reduction of α,β-Unsaturated Chromium Carbene Complexes 39
Case 8. Addition of Hydroxylamines to α,β-Unsaturated Esters 47
Case 9. Solvolysis of Electron-Deficient Norbomyl Triflates 55
Case 10 Nucleophile Versus Base Catalysis 63
Case 11. The Hydrolysis ofp-Substituted Styrene Oxides 69
Case 12. Elimination Reactions of Benzaldehyde O-Benzoyloximes 79
Case 13. Oxygen Versus Sulfur Stabilization of Carbenium Ions 87
Case 14. Cyclization of 2,3-Dibenzylidenesuccinates 97
Case 15. Oxazoline N-Oxides as Dipoles in [3+2] Cycloadditions 101
Case 16. Light-Induced Cycloadditions of N-Phthaloyl α-Amino Acids 107
Level 2 113
Case 17. Change in Rate-Determining Step in an E 1 cB Mechanism:Aminolysis of Sulfamate Esters 113
Case 18. Unusual Diels-Alder Reactivity of Acyclic 2-Azadienes 119
Case 19. Chelate-Controlled Carbonyl Addition Reactions 125
Case 20. Esterification of Carboxylic Acids with Dimethyl Carbonate and DBU 131
Case 21. A Hammett Analysis in a Multistep Reaction:Rhodium(Ⅱ)-Catalyzed Decomposition of α-Diazo Esters 139
Case 22. Tandem Cycloadditions with Nitronates 145
Case 23. Hydrolysis of 2-Aminobenzoate Esters 153
Case 24. Rearrangements of Cyclobutenones 159
Case 25. Epoxi Ester-Orthoester Rearrangement 163
Case 26. 2-Chloro-1,3,5-triazines as Activating Groups of Carboxylic Acids in the Formation of Peptide Bonds 169
Case 27. Acid-Catalyzed Isomerization of Imines 177
Case 28. A Dearomatizing Disrotatory Electrocyclic Ring Closure 183
Case 29. Stereoselective Debromination of Vicinal Dibromides 189
Case 30. Diels-Alder Reactions of N-Acyl-1,2,4,5-tetrazines 197
Case 31. Stereoselective Synthesis of 2-Acylaziridines 203
Level 3 211
Case 32. The Baylis-Hillman Reaction 211
Case 33. The Rate-Determining Step in the SNAr Reaction 217
Case 34. Helicenophanes and their Racemization 225
Case 35. Solvolysis of Vinyl Iodonium Salts 231
Case 36. Vicarious Nucleophilic Substitution 237
Case 37. Base-promoted HF Elimination from 4-Fluoro-4-(4′-nitrophenyl)butan-2-one 243
Case 38. Substitution of β-Halostyrenes by MeS- 251
Case 39. Periodinane-Mediated Cyclization of Anilides 259
Case 40. Solvolysis of 8-Deltacyclyl Brosylates 269
Subject Index 277