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Organic Syntheses, Volume 88

ISBN: 978-1-118-17397-8
528 pages
December 2011
Organic Syntheses, Volume 88 (111817397X) cover image
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.
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Editorial: Organic Syntheses: The “Gold Standard” for Experimental Synthetic Organic Chemistry 1
Rick L. Danheiser

α-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

Gram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-Bromopheneyl)Aziridine 2-Carboxylate 224
Aman A. Desai, Roberto Morán-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
Björn C. Söderberg

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. Viózquez, Gabriela Guillene, Carmen Nájera, 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. Viózquez, Gabriela Guillena, and Carmen Nájera

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

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