Description
Book SynopsisThe 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.
Table of ContentsEditorial: 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
