Description
Book SynopsisThe 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.
Table of ContentsCopper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes 1
Wei Wen Tan, Bin Wu, Ye Wei, and Naohiko Yoshikai
An Au/Zn-catalyzed Synthesis of N-Protected Indole via Annulation of N-Arylhydroxamic Acid and Alkyne 15
Xinpeng Cheng, Yanzhao Wang, and Liming Zha
Preparation of Fac-Tris(2-Phenylpyridinato) Iridium(III) 29
Kip A. Teegardin and Jimmie D. Weaver
Preparation of Cyclopent-2-enone Derivatives via the Aza-Piancatelli Rearrangement 46
Meghan F. Nichol, Luis Limon, and Javier Read de Alaniz
Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles 60
Kyle M. Lambert, Sherif A. Eldirany, James M. Bobbitt, and William F. Bailey
Copper-Catalyzed Enantioselective Hydroamination of Alkenes 80
Richard Y. Liu and Stephen L. Buchwald
Preparation of 6H-Benzo[c]chromen-6-one 97
Yang Wang, Yi Shi, and Vladimir Gevorgya
Synthesis of N-Acyl Pyridinium-N-Aminides and Their Conversion to 4-Aminooxazoles via a Gold-Catalyzed Formal (3+2)-Dipolar Cycloaddition 112
Matthew P. Ball-Jones and Paul W. Davies
Preparation of Solid Organozinc Pivalates and Their Reaction in Pd-Catalyzed Cross-Couplings 127
Mario Ellwart, Yi-Hung Chen, Carl Phillip Tüllmann, Vladimir Malakhov, and Paul Knochel
Enantioselective Synthesis of (S)-Ethyl 2-((tert-butoxycarbonyl)((tertbutyldimethylsilyl) oxy)amino)-4 oxobutanoate 142
Thibault J. Harmand, Claudia E. Murar, Hikaru Takano, and Jeffrey W. Bode
Preparation of (S)-N-Boc-5-oxaproline 157
Claudia E. Murar, Thibault J. Harmand, Hikaru Takano, and Jeffrey W. Bode
Syntheses of Substituted 2-Cyano-benzothiazoles 177
Hendryk Würfel and Dörthe Jakobi
Preparation of N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ylidene) nitramide 192
Emerson Teixeira da Silva, Adriana Marques Moraes, Adriele da Silva Araújo, and Marcus Vinícius Nora de Souza
Preparation of Alkyl Boronic Esters Using Radical-Polar Crossover Reactions of Vinylboron Ate Complexes 205
Marvin Kischkewitz and Armido Studer
Preparation of (pin)B–B(dan) 218
Hiroto Yoshida, Yuya Murashige, and Itaru Osaka
Discussion Addendum for: Preparation of a Carbazole-Based Macrocycle Via Precipitation-Driven Alkyne Metathesis 231
Christopher C. Pattillo, Morgan M. Cencer, and Jeffrey S. Moore
Hydrodecyanation by a Sodium Hydride-Iodide Composite 240
Guo Hao Chan, Derek Yiren Ong, and Shunsuke Chiba
Indole-Catalyzed Bromolactonization: Preparation of Bromolactone in Lipophilic Media 256
Zhihai Ke, Tao Chen, and Ying-Yeung Yeung
Discussion Addendum for: Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation [(E)-Methyl 3-phenyloct-2-enoate] 267
Yoshihiko Yamamoto
Modified McFadyen-Stevens Reaction for a Versatile Synthesis of Aromatic Aldehydes 276
Yuri Iwai and Jun Shimokawa
Discussion Addendum for: Facile Syntheses of Aminocyclopropanes: N,N-Dibenzyl-N-(2-ethenylcyclopropyl)amine [(Benzenemethanamine, N-(2-ethenylcyclopropyl)-N-(phenylmethyl)) 289
Armin de Meijere and Sergei I. Kozhushkov
(R)-2,2,2-Trichloro-1-phenylethyl (methylsulfonyl)oxycarbamate 310
Hélène Lebel, Henri Piras, and Johan Bartholoméüs
Large Scale Synthesis of Enantiomerically Pure (S)-3-(4-Bromophenyl)- butanoic Acid 328
J. Craig Ruble, H. George Vandeveer, and Antonio Navarro
Preparation of Tributyl(iodomethyl)stannane 345
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Stannylamine Protocol (SnAP) Reagents for the Synthesis of C–Substituted Morpholines from Aldehydes 357
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Trimethylsilyldiazo[13C]methane: A Versatile 13C-Labelling Reagent 374
Chris Nottingham and Guy C. Lloyd-Jones
Stereoretentive Iron-catalyzed Cross-coupling of an Enol Tosylate with MeMgBr 403
Takeshi Tsutsumi, Yuichiro Ashida, Hiroshi Nishikado, and Yoo Tanabe
Synthesis of Methyl 2-Bromo-3-oxocyclopent-1-ene-1-carboxylate 425
Rama Rao Tata and Michael Harmata
Discussion Addendum for: Preparation of (S)-tert-ButylPHOX and (S)-2-Allyl-2-Methylcyclohexanone 439
Alexander W. Sun and Brian M. Stoltz
Synthesis of Acyl Derivatives of Cotarnine 455
Laxmidhar Rout, Bibhuti Bhusan Parida, Ganngum Phaomei, Bertounesque Emmanuel, and Akhila Kumar Sahoo
Carbonyl-Olefin Metathesis for the Synthesis of Cyclic Olefins 472
Marc R. Becker, Katie A. Rykaczewski, Jacob R. Ludwig, and Corinna S. Schindler
Hexafluoro-2-propanol-promoted Intramolecular Friedel-Crafts Acylation 486
Rakesh H. Vekariya, Matthew C. Horton, and Jeffrey Aubé
Discussion Addendum for: Preparation of the COP Catalysts: [(S)-COP-OAc]2, [(S)-COP-Cl]2, and (S)-COP-hfacac 500
Jeffrey S. Cannon and Larry E. Overman
