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The current volume continues the tradition of the Organic Syntheses 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 pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
List of contents
Discussion Addendum for: Synthesis of Arylboronic Pinacol Esters from Corresponding Arylamines 1
Fanyang Mo, Di Qiu, and Jianbo Wang
Deaminative Functionalization of Primary Sulfonamides 12
Patrick S. Fier and Kevin M. Maloney
Synthesis of 3,6-Bis(dimethylamino)-9H-xanthen-9-one by Stepwise Chemical Redox Cycling 21
James L. Bachman, Cyprian I. Pavlich, and Eric V.Anslyn
Preparation of (-)-Levoglucosenone from Cellulose Using Sulfuric Acid in Polyethylene Glycol 38
J. Klepp, W. Dillon, Y. Lin, P. Feng, and B. W. Greatrex
Scalable Preparation of O-(Diphenylphosphinyl) hydroxylamine (DPPH) 54
Tamas Benkovics, Andrew J. Neel, Ralph Zhao, and Gregory J. Hughes
Discussion Addendum for: Dibenzo[a,e]cyclooctene: Multigram Synthesis of a Bidentate Ligand 66
Günter Helmchen
Discussion Addendum for: (S)-(-)-2-Allylcyclohexanone (2-Allylcyclohexan-1-one] 79
Manfred Braun
Synthesis of 4-Nitrophenyl (2,2,6,6-Tetramethylpiperidin-1-yl) Carbonate (NPTC) for N-Protection of L-Phenylalanine Ethyl Ester 96
Joseph R. Lizza and Peter Wipf
Discussion Addendum for: Pd-Catalyzed External-CO-Free Carbonylation: Preparation of 2,4,6-Trichlorophenyl 3,4-Dihydronaphthalene-2-Carboxylate 125
Hideyuki Konishi and Kei Manabe
From 5-Hydroxynicotinic Acid to Nitrogenous (4+3)-Cycloadducts 139
Alexander S. Harmata and Michael Harmata
Synthesis of alpha-Bromoacetyl MIDA Boronate 157
C. Frank Lee, Chieh-Hung Tien, Shinya Adachi, and Andrei K. Yudin
Synthesis of Chiral Bisoxazoline Ligands: (3aR,3a'R,8aS,8a'S)-2,2'- (cyclopropane-1,1-diyl)bis(3a,8a-dihydro-8H-indeno[1,2-d]oxazole) 172
Julie L. Hofstra, Travis J. DeLano, and Sarah E. Reisman
Synthesis of 2,5-Diaryloxadiazinones 189
Andrew V. Kelleghan, Katie A. Spence, and Neil K. Garg
Preparation of O-Pivaloyl Hydroxylamine Triflic Acid 207
Szabolcs Makai, Eric Falk, and Bill Morandi
Preparation of a Z-Iodoalkene through Stork-Zhao-Wittig Olefination, Stereo-retentive Lithium-iodine Exchange and Z-Boronic acid Pinaco Ester Synthesis 217
Mathieu A. Morin, Samantha Rohe, Cecile Elgindy, and Michael S. Sherburn
Discussion Addendum for: Synthesis of Substituted Indazoles via [3 + 2] Cycloaddition of Benzyne and Diazo Compounds 232
Anton V. Dubrovskiy and Richard C. Larock
Anhydrous, Homogeneous, Suzuki-Miyaura Cross-Coupling of Boronic Esters using Potassium Trimethylsilanolate 245
Connor P. Delaney, Ethan M. Heyboer, and Scott E. Denmark
Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M 262
Anjing Hu, Zhan-Ming Zhang, Yuanjing Xiao, and Junliang Zhang
Preparation of Asymmetric Phase-transfer Catalyst, 1,4-Bis((4S,5S)- 1,3-bis(3,5-di-tert-butylbenzyl)-4,5-diphenylimidazolidin-2-ylidene)piperazine-1,4-diium chloride 274
Esther Cai Xia Ang, Xinyi Ye, and Choon-Hong Tan
Oxidation of Aldehydes to Nitriles with an Oxoammonium Salt: Preparation of Piperonylonitrile 294
Nathaniel D. Kaetzel, Kyle M. Lambert, and Christopher B. Kelly
Preparation of 1H-Indazole-3-carbonitrile 314
Yonggang Chen, Qinghao Chen, Lushi Tan, Lu Chen, and Xiaowei Wang
Asymmetric Michael Addition of Dimethyl Malonate to 2-Cyclopenten-1-one Catalyzed by a Heterobimetallic Complex 327
Nicholas J. Fastuca, Alice R. Wong, Victor W. Mak, and Sarah E. Reisman
Discussion Addendum for: Synthesis of Et2SBr*SbCl5Br and its Use in Biomimetic Brominative Polyene Cyclizations 339
Cooper A. Taylor and Scott A. Snyder
Nickel-Catalyzed Arylboration of Cyclopentene 355
Stephen R. Sardini and M. Kevin Brown
Summary
The current volume continues the tradition of the Organic Syntheses 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 pharmaceuticals, fine chemicals, agrochemicals, and biotechnological products.
