Organic Syntheses, Volume 88

Informationen zum Autor Jonathan A. Ellman is Eugene Higgins Professor of Chemistry at Yale University. He received his B.S. in Chemistry from MIT and his PhD in Organic Chemistry from Harvard University. His research efforts are focused on the development of efficient, systematic chemical tools to establish protein function through the design and synthesis of small molecule libraries targeting protein families, methods for the asymmetric synthesis of amines, and the development of synthetic applications of C-H activation. Klappentext The current volume continues the tradition of providing significant and interesting procedures, which should prove worthwhile to many synthetic chemists working in increasingly diverse areas. Following precedent, there is no specific or central theme to this volume. Zusammenfassung The current volume continues the tradition of the Organic Synthesis series, providing carefully checked and edited experimental procedures that describe important synthetic methods, transformations, reagents, and synthetic building blocks or intermediates with demonstrated utility in organic synthesis. Inhaltsverzeichnis Editorial: Organic Syntheses: The "Gold Standard" for Experimental Synthetic Organic Chemistry 1 Rick L. Danheiser ¿-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(µ-Br)] 4 David S. Huang, Ryan J. DeLuca, and John F. Hartwig The Preparation of Amides by Copper-medicated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 14 Maxime Giguère-Bisson, Woo-Jin Yoo, and Chao-Jun Li Synthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 22 Louis-Charles Campeau and Keith Fagnou The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Animation of 2-Aminophenyl  Ketoximes 33 Carla M. Councellar, Chad C. Eichman, Brenda C. Wray, Eric R. Welin, and James P. Stambuli The Preparation of (2R,5S)-2-t-Butyl-3,5-Dimethylimidazolidin-4-One 42 Thomas H. Graham, Benjamin D. Horning, and David W. C. MacMillan Synthesis of Et2SB¿SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 54 Scott A. Snyder and Daniel S. Treitler Discussion Addendum for: Asymmetric Synthesis of (M)-2- Hydroxymethyl-1-(2-Hydroxy-3,6-Dimethylphenyl)Naphthalene via a Configurationally Unstable Biaryl Lactone 70 G. Bringmann, T. A. M. Gulder, and T. Gulder Synthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 79 Yasunori Yamamoto, Juugaku Sigai, Miho Takizawa, and Norio Miyaura Synthesis of (+)-B-Allyldiisopinocampheylborane and It Reaction with Aldehydes 87 Huikai Sun and William R. Roush Discussion Addendum for: Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene 102 Scott E. Denmark and Jack Hung-Chang Liu The Preparation of Cyclohept-4-Enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 109 Paul A. Wender, Adam B. Lesser, and Lauren E. Sirois Organocatalytic Enantioselective Synthesis of Bicyclic ß-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 121 Henry Nguyen, Seongho Oh, Huda Henry-Riyad, Diana Sepulveda, and Daniel Romo Phosphine-Catalyzed [3 + 2) Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 138 Ian P. Andrews and Ohyun Kwon Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxy-Phosphinyl)Acetate 152 Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama Discussion Addendum for: 5-ENDO-TRIG Cyclization of 1,1-Difluoro-1-Alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole (1H-Indol...

Inhaltsverzeichnis

Editorial: Organic Syntheses: The "Gold Standard" for Experimental Synthetic Organic Chemistry 1
Rick L. Danheiser
 
±-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(µ-Br)] 4
David S. Huang, Ryan J. DeLuca, and John F. Hartwig
 
The Preparation of Amides by Copper-medicated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 14
Maxime Giguère-Bisson, Woo-Jin Yoo, and Chao-Jun Li
 
Synthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 22
 
Louis-Charles Campeau and Keith Fagnou
 
The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Animation of 2-Aminophenyl Ketoximes 33
Carla M. Councellar, Chad C. Eichman, Brenda C. Wray, Eric R. Welin, and James P. Stambuli
 
The Preparation of (2R,5S)-2-t-Butyl-3,5-Dimethylimidazolidin-4-One 42
Thomas H. Graham, Benjamin D. Horning, and David W. C. MacMillan
 
Synthesis of Et2SB*SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 54
Scott A. Snyder and Daniel S. Treitler
 
Discussion Addendum for: Asymmetric Synthesis of (M)-2- Hydroxymethyl-1-(2-Hydroxy-3,6-Dimethylphenyl)Naphthalene via a Configurationally Unstable Biaryl Lactone 70
G. Bringmann, T. A. M. Gulder, and T. Gulder
 
Synthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 79
Yasunori Yamamoto, Juugaku Sigai, Miho Takizawa, and Norio Miyaura
 
Synthesis of (+)-B-Allyldiisopinocampheylborane and It Reaction with Aldehydes 87
Huikai Sun and William R. Roush
 
Discussion Addendum for: Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene 102
Scott E. Denmark and Jack Hung-Chang Liu
 
The Preparation of Cyclohept-4-Enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 109
Paul A. Wender, Adam B. Lesser, and Lauren E. Sirois
 
Organocatalytic Enantioselective Synthesis of Bicyclic ß-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 121
Henry Nguyen, Seongho Oh, Huda Henry-Riyad, Diana Sepulveda, and Daniel Romo
 
Phosphine-Catalyzed [3 + 2) Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 138
Ian P. Andrews and Ohyun Kwon
 
Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxy-Phosphinyl)Acetate 152
Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama
 
Discussion Addendum for: 5-ENDO-TRIG Cyclization of 1,1-Difluoro-1-Alkenes: Synthesis of 3-Butyl-2-Fluoro-1-Tosylindole (1H-Indole, 3-Butyl-2-Fluoro-1-[(4-Methylphenyl)Sulfonyl-) 162
Junji Ichikawa
 
Preparation of a Thrifluoromethyl Transfer Agent: 1-Trifloromethyl-1,3-Dihydro-3,3-Dimenthyl-1,2-Benziodoxole 168
Patrick Eisenberger, Iris Kieltsch, Raffael Koller, Kyrill Stanek, and Antonio Tongni
 
Synthesis of (S,S)-Diisopropyl Tartrate (E)-Crothylboronate and Its Reaction with Aldehydes: (2R,3R,4R)-1,2-Dideoxy-2-Ethenyl-4,5,-O-(1-Methylethylidene)-Xylitol 181
Huikai Sun and William R. Roush
 
Discussion Addendum for: 4-Methoxy-4'-Nitrophenyl. Recent Advances in the Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis 197
Robert M. Williams
 
Discussion Addendum for: Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene 202
Norio Miyaura
 
Discussion Addendum for: Palladium (0)-Catalyzed Reaction of 9-Alkyl-9-Borabicyclo[3.3.1]Nonane with 1-Bromo-1-Phenylthioethene: 4-(3-Cyclohexenyl )-2-Phenylthio-1-1-Butene 207
Norio Miyaura
 
Preparation of Isopropyl 2-Diazoacetyl(Phenyl)Carbamate 212
Hubert Muchalski, Amanda B. Doody, Timothy L. Troyer, and Jeffrey N. Johnson
 

Produktdetails

• Autoren: Ellman, Jonathan A Ellman, Jonathan A. Ellman, Jonathan A. (University of Pittsburgh Ellman, Wayland E. Noland, Peter Wipf
• Mitarbeit: Waylan E Noland (Herausgeber), Wayland E Noland (Herausgeber), Ellman Jonathan A. (Herausgeber), Wayland E. Noland (Herausgeber)
• Verlag: Wiley, John and Sons Ltd
• Sprache: Englisch
• Produktform: Fester Einband
• Erschienen: 30.12.2011
• EAN: 9781118173978
• ISBN: 978-1-118-17397-8
• Seiten: 528
• Serien: Organic Syntheses; Organic Syntheses
• Themen: Naturwissenschaften, Medizin, Informatik, Technik > Chemie > Physikalische Chemie; Chemie, ORGANOMETALLIC CHEMISTRY, chemistry, Organische Synthese, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren, Organometallchemie