Organic Syntheses: 88

Organic Syntheses: 88

By: Jonathan A. Ellman (editor)Hardback

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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. These significant and interesting procedures should prove worthwhile to many synthetic chemists working in increasingly diverse areas. A trusted guide for professionals in organic and medicinal chemistry in academia, government, and industries, including phar-maceuticals, fine chemicals, agrochemicals, and biotech.


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( -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 Giguere-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 Gram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-Bromopheneyl)Aziridine 2-Carboxylate 224 Aman A. Desai, Roberto Moran-Ramallal, and William D. Wulff Cu-Catalyzed Azide-Alkyne Cycloaddition: Preparation of Tris((1-Benzyl-1H-1,2,3-Triazolyl )Methyl)Amine 238 Jason E. Hein, Larissa B. Krasnova, Masayuki Iwasaki, and Valery V. Fokin Lithiated Primary Alkyl Carbamates for the Homologation of Boronic Esters Matthew P. Webster, Benjamin M. Partridge, and Varinder K. Aggarwal Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-Diene 260 Sandro Cacchi, Enrico Morera, and Giorgio Ortar Discussion Addendum for: Synthesis of Indoles by Palladium-Catalyzed Reductive N-Heteroannulation of 2-Nitrostyrenes: Methyl Indole-4-Carboxylate 291 Bjorn C. Soderberg An Economical Synthesis of 4-Trimethysilyl-2-Butyn-1-OL 296 Alexander N. Wein, Rongbiao Tong, and Frank E. McDonald Silver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis of Allengic Sulfones 309 Michael Harmata, Zhengxin Cai and Chaofeng Huang (Sa,S)-N-[2 -(Methylphenylsulfonamido)-1-1 -Binaphthyl-2-YL]Pyrrolidine-2-Carboxamide: An Organocatalyst for the Direct Aldol Reaction 317 Santiago F. Viozquez, Gabriela Guillene, Carmen Najera, Ben Bradshaw, Gorka Etxebarria-Jardi, and Josep Bonjoch Synthesis of (S)-8a-Methyl-3,4,8,8a-Tetrahydro-1,6-(2H,7H)-Naphthalenedione via N-Tosyl-(Sa)-Binam-L-Pholinamide Organocatalysis 330 Ben Bradshaw, Gorka Etxebarria-Jardi, Josep Bonjoch, Santiago F. Viozquez, Gabriela Guillena, and Carmen Najera Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes 342 Robert J. Ely and James P. Morken Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-Oxo-5-Heptynyl)-1-3-Dithiane 353 Marilda P. Lisboa, Tunf T. Hoang, and Gregory B. Dudley Synthesis and Diasteroselective Aldol Reactions of a Thiazolidinethione Chiral Auxiliary 364 Michael T. Crimmins, Hamish S. Christie, and Colin O. Hughes Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes: 3-Methyl-2-(Trimethylsilyl)Indole 377 Yu Chen, Nataliya A. Markina, Tuanli Yao, and Richard C. Larock An Intramolecular Amination of Aryyl Halides with a Combination of Copper (I) and Cesium Acetate: Preparation of 5,6-Dimethoxyindole-1,2-Dicarboxylic Acid 1-Benzyl Ester 2-Methyl Ester 388 Toshiharu Noji, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama Ligand-Free Copper(II) Oxide Nanoparticles-Catalyzed Synthesis of Substituted Benzoxazoles 398 Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy (R)-3,3 -Bis(9-Phenanthyryl)-1,1 -Binaphthalene-2,2 -Diyl Hydrogen Phosphate 406 Wenhao Hu, Jing Zhou, Xinfang Xu, Weijun Liu, and Liuzhu Gong Enantioselective Three-Component Reaction for the Preparation of ss-Amino-a-Hydroxy Esters 418 Jing Zhou, Xinfang Xu, and Wenhao Hu Mild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz s Reagent) 427 Matthew W. Leighty, Jared T. Spletstoser, and Gunda I. Georg

Product Details

  • ISBN13: 9781118173978
  • Format: Hardback
  • Number Of Pages: 528
  • ID: 9781118173978
  • weight: 832
  • ISBN10: 111817397X

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