Organic Syntheses, Volume 88

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.

• Editorial: Organic Syntheses: The “Gold Standard” for Experimental Synthetic Organic Chemistry 1Rick L. Danheiser α-Arylation of Esters Catalyzed by the Pd(I) Dimer [P(t-Bu)3Pd(µ-Br)] 4David S. Huang, Ryan J. DeLuca, and John F. HartwigThe Preparation of Amides by Copper-medicated Oxidative Coupling of Aldehydes and Amine Hydrochloride Salts 14Maxime Giguère-Bisson, Woo-Jin Yoo, and Chao-Jun LiSynthesis of 2-Aryl Pyridines by Palladium-Catalyzed Direct Arylation of Pyridine N-Oxides 22Louis-Charles Campeau and Keith Fagnou The Preparation of Indazoles via Metal Free Intramolecular Electrophilic Animation of 2-Aminophenyl  Ketoximes 33Carla M. Councellar, Chad C. Eichman, Brenda C. Wray, Eric R. Welin, and James P. StambuliThe Preparation of (2R,5S)-2-t-Butyl-3,5-Dimethylimidazolidin-4-One 42Thomas H. Graham, Benjamin D. Horning, and David W. C. MacMillanSynthesis of Et2SB•SbCl5Br and Its Use in Biomimetic Brominative Polyene Cyclizations 54Scott A. Snyder and Daniel S. TreitlerDiscussion Addendum for: Asymmetric Synthesis of (M)-2- Hydroxymethyl-1-(2-Hydroxy-3,6-Dimethylphenyl)Naphthalene via a Configurationally Unstable Biaryl Lactone 70G. Bringmann, T. A. M. Gulder, and T. GulderSynthesis of Lithium 2-Pyridyltriolborate and Its Cross-Coupling Reaction with Aryl Halides 79Yasunori Yamamoto, Juugaku Sigai, Miho Takizawa, and Norio MiyauraSynthesis of (+)-B-Allyldiisopinocampheylborane and It Reaction with Aldehydes 87Huikai Sun and William R. RoushDiscussion Addendum for: Palladium-Catalyzed Cross-Coupling of (Z)-1-Heptenyldimethylsilanol with 4-Iodoanisole: (Z)-(1-Heptenyl)-4-Methoxybenzene 102Scott E. Denmark and Jack Hung-Chang LiuThe Preparation of Cyclohept-4-Enones by Rhodium-Catalyzed Intermolecular [5+2] Cycloaddition 109Paul A. Wender, Adam B. Lesser, and Lauren E. SiroisOrganocatalytic Enantioselective Synthesis of Bicyclic ß-Lactones from Aldehyde Acids via Nucleophile-Catalyzed Aldol-Lactonization (NCAL) 121Henry Nguyen, Seongho Oh, Huda Henry-Riyad, Diana Sepulveda, and Daniel RomoPhosphine-Catalyzed [3 + 2) Annulation: Synthesis of Ethyl 5-(tert-Butyl)-2-Phenyl-1-Tosyl-3-Pyrroline-3-Carboxylate 138Ian P. Andrews and Ohyun KwonPreparation of Horner-Wadsworth-Emmons Reagent: Methyl 2-Benzyloxycarbonylamino-2-(Dimethoxy-Phosphinyl)Acetate 152Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, and Hidetoshi TokuyamaDiscussion 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-) 162Junji IchikawaPreparation of a Thrifluoromethyl Transfer Agent: 1-Trifloromethyl-1,3-Dihydro-3,3-Dimenthyl-1,2-Benziodoxole 168Patrick Eisenberger, Iris Kieltsch, Raffael Koller, Kyrill Stanek, and Antonio TongniSynthesis 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 181Huikai Sun and William R. RoushDiscussion Addendum for: 4-Methoxy-4’-Nitrophenyl. Recent Advances in the Stille Biaryl Coupling Reaction and Applications in Complex Natural Products Synthesis 197Robert M. WilliamsDiscussion Addendum for: Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene 202Norio MiyauraDiscussion 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  207Norio MiyauraPreparation of Isopropyl 2-Diazoacetyl(Phenyl)Carbamate 212Hubert Muchalski, Amanda B. Doody, Timothy L. Troyer, and Jeffrey N. JohnsonGram Scale Catalytic Asymmetric Aziridination: Preparation of (2R,3R)-Ethyl 1-Benzhydryl-3-(4-Bromopheneyl)Aziridine 2-Carboxylate 224Aman A. Desai, Roberto Morán-Ramallal, and William D. WulffCu-Catalyzed Azide-Alkyne Cycloaddition: Preparation of Tris((1-Benzyl-1H-1,2,3-Triazolyl )Methyl)Amine 238Jason E. Hein, Larissa B. Krasnova, Masayuki Iwasaki, and Valery V. FokinLithiated Primary Alkyl Carbamates for the Homologation of Boronic EstersMatthew P. Webster, Benjamin M. Partridge, and Varinder K. AggarwalDiscussion Addendum for: Palladium-Catalyzed Reduction of Vinyl Trifluoromethanesulfonates to Alkenes: Cholesta-3,5-Diene 260Sandro Cacchi, Enrico Morera, and Giorgio OrtarDiscussion Addendum for: Synthesis of Indoles by Palladium-Catalyzed Reductive N-Heteroannulation of 2-Nitrostyrenes: Methyl Indole-4-Carboxylate 291Björn C. SöderbergAn Economical Synthesis of 4-Trimethysilyl-2-Butyn-1-OL 296Alexander N. Wein, Rongbiao Tong, and Frank E. McDonaldSilver-Catalyzed Rearrangement of Propargylic Sulfinates: Synthesis of Allengic Sulfones 309Michael 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 317Santiago F. Viózquez, Gabriela Guillene, Carmen Nájera, Ben Bradshaw, Gorka Etxebarria-Jardi, and Josep BonjochSynthesis of (S)-8a-Methyl-3,4,8,8a-Tetrahydro-1,6-(2H,7H)-Naphthalenedione via N-Tosyl-(Sa)-Binam-L-Pholinamide Organocatalysis 330Ben Bradshaw, Gorka Etxebarria-Jardi, Josep Bonjoch, Santiago F. Viózquez, Gabriela Guillena, and Carmen NájeraStereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes 342Robert J. Ely and James P. MorkenTandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Triflates: 2-Methyl-2-(1-Oxo-5-Heptynyl)-1-3-Dithiane 353Marilda P. Lisboa, Tunf T. Hoang, and Gregory B. DudleySynthesis and Diasteroselective Aldol Reactions of a Thiazolidinethione Chiral Auxiliary 364Michael T. Crimmins, Hamish S. Christie, and Colin O. HughesSynthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes: 3-Methyl-2-(Trimethylsilyl)Indole 377Yu Chen, Nataliya A. Markina, Tuanli Yao, and Richard C. LarockAn 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 388Toshiharu Noji, Kentaro Okano, Tohru Fukuyama, and Hidetoshi TokuyamaLigand-Free Copper(II) Oxide Nanoparticles-Catalyzed Synthesis of Substituted Benzoxazoles 398Prasenjit Saha, Md Ashif Ali, and Tharmalingam Punniyamurthy(R)-3,3’-Bis(9-Phenanthyryl)-1,1’-Binaphthalene-2,2’-Diyl Hydrogen Phosphate 406Wenhao Hu, Jing Zhou, Xinfang Xu, Weijun Liu, and Liuzhu GongEnantioselective Three-Component Reaction for the Preparation of ß-Amino-a-Hydroxy Esters 418Jing Zhou, Xinfang Xu, and Wenhao HuMild Conversion of Tertiary Amides to Aldehydes Using Cp2Zr(H)Cl (Schwartz’s Reagent) 427Matthew W. Leighty, Jared T. Spletstoser, and Gunda I. Georg