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Organic Syntheses, Volume 88
Jonathan A. Ellman (Edited by), Ellman (Author)
9781118173978, Wiley
Hardback, published 30 December 2011
528 pages
23.6 x 16 x 3.2 cm, 0.844 kg
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 α-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(µ-Br)] 4 The Preparation of Amides by Copper-medicated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 14 Synthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 22 The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Animation of 2-Aminophenyl Ketoximes 33 The Preparation of (2R,5S)-2-t-Butyl-3,5-Dimethylimidazolidin-4-One 42 Synthesis of Et2SB•SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 54 Discussion Addendum for: Asymmetric Synthesis of (M)-2- Hydroxymethyl-1-(2-Hydroxy-3,6-Dimethylphenyl)Naphthalene via a Configurationally Unstable Biaryl Lactone 70 Synthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 79 Synthesis of (+)-B-Allyldiisopinocampheylborane and It Reaction with Aldehydes 87 Discussion Addendum for: Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene 102 The Preparation of Cyclohept-4-Enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 109 Organocatalytic Enantioselective Synthesis of Bicyclic ß-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 121 Phosphine-Catalyzed [3 + 2) Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 138 Preparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxy-Phosphinyl)Acetate 152 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 Preparation of a Thrifluoromethyl Transfer Agent: 1-Trifloromethyl-1,3-Dihydro-3,3-Dimenthyl-1,2-Benziodoxole 168 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 Discussion Addendum for: 4-Methoxy-4’-Nitrophenyl. Recent Advances in the Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis 197 Discussion Addendum for: Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene 202 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 Preparation of Isopropyl 2-Diazoacetyl(Phenyl)Carbamate 212 Gram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-Bromopheneyl)Aziridine 2-Carboxylate 224 Cu-Catalyzed Azide-Alkyne Cycloaddition: Preparation of Tris((1-Benzyl-1H-1,2,3-Triazolyl )Methyl)Amine 238 Lithiated Primary Alkyl Carbamates for the Homologation of Boronic Esters Discussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-Diene 260 Discussion Addendum for: Synthesis of Indoles by Palladium-Catalyzed Reductive N-Heteroannulation of 2-Nitrostyrenes: Methyl Indole-4-Carboxylate 291 An Economical Synthesis of 4-Trimethysilyl-2-Butyn-1-OL 296 Silver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis of Allengic Sulfones 309 (Sa,S)-N-[2’-(Methylphenylsulfonamido)-1-1’-Binaphthyl-2-YL]Pyrrolidine-2-Carboxamide: An Organocatalyst for the Direct Aldol Reaction 317 Synthesis of (S)-8a-Methyl-3,4,8,8a-Tetrahydro-1,6-(2H,7H)-Naphthalenedione via N-Tosyl-(Sa)-Binam-L-Pholinamide Organocatalysis 330 Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes 342 Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-Oxo-5-Heptynyl)-1-3-Dithiane 353 Synthesis and Diasteroselective Aldol Reactions of a Thiazolidinethione Chiral Auxiliary 364 Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes: 3-Methyl-2-(Trimethylsilyl)Indole 377 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 Ligand-Free Copper(II) Oxide Nanoparticles-Catalyzed Synthesis of Substituted Benzoxazoles 398 (R)-3,3’-Bis(9-Phenanthyryl)-1,1’-Binaphthalene-2,2’-Diyl Hydrogen Phosphate 406 Enantioselective Three-Component Reaction for the Preparation of ß-Amino-a-Hydroxy Esters 418 Mild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz’s Reagent) 427
Rick L. Danheiser
David S. Huang, Ryan J. DeLuca, and John F. Hartwig
Maxime Giguère-Bisson, Woo-Jin Yoo, and Chao-Jun Li
Louis-Charles Campeau and Keith Fagnou
Carla M. Councellar, Chad C. Eichman, Brenda C. Wray, Eric R. Welin, and James P. Stambuli
Thomas H. Graham, Benjamin D. Horning, and David W. C. MacMillan
Scott A. Snyder and Daniel S. Treitler
G. Bringmann, T. A. M. Gulder, and T. Gulder
Yasunori Yamamoto, Juugaku Sigai, Miho Takizawa, and Norio Miyaura
Huikai Sun and William R. Roush
Scott E. Denmark and Jack Hung-Chang Liu
Paul A. Wender, Adam B. Lesser, and Lauren E. Sirois
Henry Nguyen, Seongho Oh, Huda Henry-Riyad, Diana Sepulveda, and Daniel Romo
Ian P. Andrews and Ohyun Kwon
Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama
Junji Ichikawa
Patrick Eisenberger, Iris Kieltsch, Raffael Koller, Kyrill Stanek, and Antonio Tongni
Huikai Sun and William R. Roush
Robert M. Williams
Norio Miyaura
Norio Miyaura
Hubert Muchalski, Amanda B. Doody, Timothy L. Troyer, and Jeffrey N. Johnson
Aman A. Desai, Roberto Morán-Ramallal, and William D. Wulff
Jason E. Hein, Larissa B. Krasnova, Masayuki Iwasaki, and Valery V. Fokin
Matthew P. Webster, Benjamin M. Partridge, and Varinder K. Aggarwal
Sandro Cacchi, Enrico Morera, and Giorgio Ortar
Björn C. Söderberg
Alexander N. Wein, Rongbiao Tong, and Frank E. McDonald
Michael Harmata, Zhengxin Cai and Chaofeng Huang
Santiago F. Viózquez, Gabriela Guillene, Carmen Nájera, Ben Bradshaw, Gorka Etxebarria-Jardi, and Josep Bonjoch
Ben Bradshaw, Gorka Etxebarria-Jardi, Josep Bonjoch, Santiago F. Viózquez, Gabriela Guillena, and Carmen Nájera
Robert J. Ely and James P. Morken
Marilda P. Lisboa, Tunf T. Hoang, and Gregory B. Dudley
Michael T. Crimmins, Hamish S. Christie, and Colin O. Hughes
Yu Chen, Nataliya A. Markina, Tuanli Yao, and Richard C. Larock
Toshiharu Noji, Kentaro Okano, Tohru Fukuyama, and Hidetoshi Tokuyama
Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy
Wenhao Hu, Jing Zhou, Xinfang Xu, Weijun Liu, and Liuzhu Gong
Jing Zhou, Xinfang Xu, and Wenhao Hu
Matthew W. Leighty, Jared T. Spletstoser, and Gunda I. Georg
Subject Areas: Chemistry [PN]
