Organocatalytic Cycloadditions for Synthesis of Carbo- and Heterocycles

Content: Preface ix 1 Introduction to Organocatalytic Cycloaddition Reaction 1Yin Wei and Min Shi 1.1 General Introduction 1 1.2 General Mechanistic Insights into Cycloadditions Catalyzed by Nucleophilic Organocatalysts 2 1.2.1 Mechanisms for Common Organoamine  -catalyzed Cycloaddition Reactions 2 1.2.2 Mechanisms for Common Organophosphine  -catalyzed Cycloaddition Reactions 11 1.2.3 Cycloaddition Reaction Modes Influenced By Catalysts 19 References 22 2 Organoamines  -catalyzed Cycloadditions 25Mei  -Xin Zhao and Min Shi 2.1 Introduction 25 2.2 [2+2] Cycloadditions 26 2.2.1 Ketene and Their Analogs Involved [2+2] Cycloadditions 26 2.2.1.1 [2+2] Cycloadditions for the Synthesis of     -Lactones 26 2.2.1.2 [2+2] Cycloadditions for the Synthesis of     ]Lactams 39 2.2.1.3 [2+2] Cycloadditions for the Synthesis of Other Four  ]membered Heterocycles 48 2.2.2 Allenoates and Their Analogs Involved [2+2] Cycloadditions 50 2.2.2.1 [2+2] Cycloadditions of Allenoates and Their Analogs with Imines 51 2.2.2.2 [2+2] Cycloadditions of Allenoates with Ketones 52 2.2.2.3 [2+2] Cycloadditions of Allenoates with Other Activated Double Bonds 56 2.3 [3+2] Cycloadditions 57 2.3.1 Ketenes and Their Analogs Involved [3+2] Cycloadditions 57 2.3.2 MBH Adducts Derivatives (MBHADs) Involved [3+2] Cycloadditions 59 2.3.3 Other Substrates Involved [3+2] Cycloadditions 67 2.4 [4+2] Cycloadditions 70 2.4.1 Ketene  ]involved [4+2] Cycloadditions 70 2.4.1.1 Ketene as Dienophile  ]involved [4+2] Cycloadditions 70 2.4.1.2 Vinyl Ketene as Diene  ]Involved [4+2] Cycloadditions 83 2.4.2 Allenoates Involved [4+2] Cycloadditions 86 2.4.2.1 Allenoates Acting as a Two  ]carbon Synthon in [4+2] Cycloadditions 86 2.4.2.2 Allenoate Acting as a Four  ]carbon Synthon in [4+2] Cycloadditions 97 2.4.3 MBHADs Involved [4+2] Cycloaddition 99 2.5 Other Cycloaddition Reactions 102 2.5.1 [2+1] Cycloadditions 102 2.5.2 [3+3] Formal Cycloadditions 107 2.5.3 Domino Reactions 117 2.5.4 Miscellaneous Cycloaddition Reactions 125 2.6 Summary 131 References 132 3 Organophosphines  -Catalyzed Cycloaddition Reactions 141Yin Wei and Min Shi 3.1 Introduction 141 3.2 Phosphine  ]catalyzed [2+2] Cycloaddition Reactions 142 3.3 Phosphine  ]catalyzed [3+n] Cycloaddition 145 3.3.1 Phosphine  ]catalyzed [3+2] Cycloaddition 145 3.3.1.1 Phosphine  ]catalyzed [3+2] Cycloaddition of Allenes with Alkenes and its Asymmetric Variant 145 3.3.1.2 Phosphine  ]catalyzed [3+2] Cycloaddition of Allenes with Imines and its Asymmetric Variant 161 3.3.1.3 Phosphine  ]catalyzed [3+2] Cycloaddition of Allenes with Other Electrophiles 171 3.3.1.4 Phosphine  ]catalyzed [3+2] Cycloaddition of Morita   Baylis   Hillman Alcohol Derivatives (MBHADs) with Electrophiles and its Asymmetric Variant 173 3.3.1.5 Phosphine  -catalyzed [3+2] Cycloaddition of Activated Alkynes with Electrophiles and its Asymmetric Variant 181 3.3.2 Phosphine  ]catalyzed [3+3] Cycloaddition of Electron  ]deficient     -systems with Electrophiles and its Asymmetric Variant 184 3.4 Phosphine  ]catalyzed [4+n] Cycloaddition 188 3.4.1 Phosphine  ]catalyzed [4+2] Cycloaddition and its Asymmetric Variant 188 3.4.1.1 Phosphine  -catalyzed [4+2] Cycloaddition of Allenes with Other Electrophiles and its Asymmetric Variant 188 3.4.1.2 Phosphine  -catalyzed [4+2] Cycloaddition of Alkynes with Other Electrophiles 201 3.4.2 Phosphine  -catalyzed [4+1] Cycloaddition and its Asymmetric Variant 202 3.4.3 Phosphine  -catalyzed [4+3] Cycloaddition and its Asymmetric Variant 208 3.5 Phosphine  -catalyzed Domino Reactions 212 3.6 Miscellaneous Reactions 228 3.7 Summary 232 References 232 4 N  ]Heterocyclic Carbenes Catalyzed Cycloadditions 237Jun Zhang and Min Shi 4.1 Introduction 237 4.2 NHC  ]catalyzed [4+2] Cycloaddition Reaction 237 4.3 NHC  ]catalyzed [2+2] Cycloaddition Reaction 276 4.4 NHC  -catalyzed [3+2] Cycloaddition Reaction 284 4.5 NHC  -catalyzed [2+2+2] Cycloaddition Reaction 297 4.6 NHC  -catalyzed Domino Reactions 302 4.7 Summary 305 References 305 5 Synthetic Transformations of Organocatalytic Cycloadducts 309Yin Wei and Min Shi 5.1 Introduction 309 5.2 Synthetic Applications of Organoamine  -catalyzed Cycloaddition Reactions 309 5.2.1 Synthetic Applications of [2+2] Cycloadduct     -Lactones 309 5.2.2 Total Synthesis of Schulzeines 315 5.2.3 Total synthesis of HPA  -12 319 5.2.4 Total Syntheses of Inthomycins 320 5.2.5 Total Synthesis of Siphonarienal 324 5.2.6 Total Syntheses of Siphonarienolone and Siphonarienedione 325 5.2.7 Total Synthesis of (+)  -Maculalactone A 326 5.2.8 Synthesis of the C21   C34  -segment of Aplyronines 327 5.2.9 Formal Synthesis of the   1a Adrenergic Receptor Antagonist 330 5.2.10 Formal Synthesis of Calyxin I 332 5.2.11 Formal Synthesis of Platencin 332 5.2.12 Total Synthesis of (   )  -Patchouli Alcohol 335 5.3 Synthetic Applications of OrganoPhosphine  -catalyzed Cycloaddition Reactions 336 5.3.1 Synthesis of Pentabromopseudilin 336 5.3.2 Total Synthesis of (   )  -Hinesol 338 5.3.3 Total Synthesis of (+/-)  -Hirsutene 339 5.3.4 Total Synthesis of (+/-)  -Ricciocarpin A 340 5.3.5 Total Synthesis of (+)  -Geniposide 342 5.3.6 Formal Synthesis of (+/-)  -Allosecurinine 342 5.3.7 Formal Synthesis of (+)  -Trachelanthamidine 344 5.3.8 Total Synthesis of (+)  -Ibophyllidine 345 5.3.9 Total Synthesis of (   )  -Actinophyllic Acid 346 5.3.10 Formal Synthesis of (+)  -Alstonerine 349 5.3.11 Total Synthesis of (+)  -Hirsutine 351 5.3.12 Formal Synthesis of Reserpine 352 5.3.13 Other Synthetic Applications of Phosphine  -catalyzed [3+2] Cycloadditions 354 5.3.14 Synthetic Applications of Phosphine  -catalyzed [3+3] Cycloaddition 358 5.3.15 Synthetic Applications of Phosphine  -catalyzed [4+2] Cycloaddition 359 5.3.16 Synthetic Applications of Phosphine  -catalyzed [4+1] Cycloaddition 364 5.3.17 Synthetic Applications of Phosphine  -catalyzed [4+3] Cycloaddition 364 5.4 Summary 365 References 365 Index 369