A Publication
of Reliable Methods
for the Preparation
of Organic Compounds
Annual Volume
Volume 95 (2018)
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Synthesis of Acyl Derivatives of Cotarnine
Laxmidhar Rout, Bibhuti Bhusan Parida, Ganngum Phaomei, Bertounesque Emmanuel, and Akhila Kumar Sahoo
Org. Synth. 2018, 95, 455
DOI: 10.15227/orgsyn.095.0455
Checked by: Lee Mains, Lauren Markham, Austin Medley, and John L. Wood

Reaction scheme
Discussion Addendum for: Preparation of (S)-tert-ButylPHOX and (S)-2-Allyl-2-Methylcyclohexanone
Alexander W. Sun and Brian M. Stoltz
Org. Synth. 2018, 95, 439
DOI: 10.15227/orgsyn.095.0439

Reaction scheme
Synthesis of Methyl 2-Bromo-3-oxocyclopent-1-ene-1-carboxylate
Rama Rao Tata and Michael Harmata
Org. Synth. 2018, 95, 425
DOI: 10.15227/orgsyn.095.0425
Checked by: Leonardo J. Nannini and Erick M. Carreira

Reaction scheme
Stereoretentive Iron-catalyzed Cross-coupling of an Enol Tosylate with MeMgBr
Takeshi Tsutsumi, Yuichiro Ashida, Hiroshi Nishikado, and Yoo Tanabe
Org. Synth. 2018, 95, 403
DOI: 10.15227/orgsyn.095.0403
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
Trimethylsilyldiazo[13C]methane: A Versatile 13C-Labelling Reagent
Chris Nottingham and Guy C. Lloyd-Jones
Org. Synth. 2018, 95, 374
DOI: 10.15227/orgsyn.095.0374
Checked by: Bachir Latli and Chris Senanayake

Reaction scheme
Stannylamine Protocol (SnAP) Reagents for the Synthesis of C-Substituted Morpholines from Aldehydes
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Org. Synth. 2018, 95, 357
DOI: 10.15227/orgsyn.095.0357
Checked by: Cedric Hervieu, Estíbaliz Merino, and Cristina Nevado

Reaction scheme
Preparation of Tributyl(iodomethyl)stannane
Michael U. Luescher, Chalupat Jindakun, and Jeffrey W. Bode
Org. Synth. 2018, 95, 345
DOI: 10.15227/orgsyn.095.0345
Checked by: Rahul Mondal, Estíbaliz Merino, and Cristina Nevado

Reaction scheme
Large Scale Synthesis of Enantiomerically Pure (S)-3-(4-Bromophenyl)butanoic Acid
Craig Ruble, H. George Vandeveer, and Antonio Navarro
Org. Synth. 2018, 95, 328
DOI: 10.15227/orgsyn.095.0328
Checked by: Vignesh Palani and Richmond Sarpong

Reaction scheme
(R)-2,2,2-Trichloro-1-phenylethyl (methylsulfonyl)­oxycarbamate
Hélène Lebel, Henri Piras, and Johan Bartholoméüs
Org. Synth. 2018, 95, 310
DOI: 10.15227/orgsyn.095.0310
Checked by: Mario Leypold and Mohammad Movassaghi

Reaction scheme
Discussion Addendum for: Facile Syntheses of Aminocyclopropanes: N,N-Dibenzyl-N-(2-ethenylcyclopropyl)amine [Benzenemethanamine, N-(2-ethenylcyclopropyl)-N-(phenylmethyl)]
Armin de Meijere and Sergei I. Kozhushkov
Org. Synth. 2018, 95, 289
DOI: 10.15227/orgsyn.095.0289
Original Article: Org. Synth. 2005, 81, 14

Reaction scheme
Modified McFadyen-Stevens Reaction for a Versatile Synthesis of Aromatic Aldehydes
Yuri Iwai and Jun Shimokawa
Org. Synth. 2018, 95, 276
DOI: 10.15227/orgsyn.095.0276

Reaction scheme
Discussion Addendum for: Stereoselective Synthesis of 3-Arylacrylates by Copper-Catalyzed Syn Hydroarylation [(E)-Methyl 3-phenyloct-2-enoate]
Yoshihiko Yamamoto
Org. Synth. 2018, 95, 267
DOI: 10.15227/orgsyn.095.0267
Original Article: Org. Synth. 2010, 87, 53

Reaction scheme
Indole-Catalyzed Bromolactonization: Preparation of Bromolactone in Lipophilic Media
Zhihai Ke, Tao Chen, and Ying-Yeung Yeung
Org. Synth. 2018, 95, 256
DOI: 10.15227/orgsyn.095.0256
Checked by: Zhaobin Han and Kuiling Ding

Reaction scheme
Hydrodecyanation by a Sodium Hydride-Iodide Composite
Guo Hao Chan, Derek Yiren Ong, and Shunsuke Chiba
Org. Synth. 2018, 95, 240
DOI: 10.15227/orgsyn.095.0240
Checked by: Joyce Leung and Chris Senanayake

Reaction scheme
Discussion Addendum for: Preparation of a Carbazole-Based Macrocycle Via Precipitation-Driven Alkyne Metathesis
Christopher C. Pattillo, Morgan M. Cencer, and Jeffrey S. Moore
Org. Synth. 2018, 95, 231
DOI: 10.15227/orgsyn.095.0231
Original Article: Org. Synth. 2007, 84, 177

Reaction scheme
Preparation of (pin)B-B(dan)
Hiroto Yoshida, Yuya Murashige, and Itaru Osaka
Org. Synth. 2018, 95, 218
DOI: 10.15227/orgsyn.095.0218
Checked by: Feng Peng and Kevin Campos

Reaction scheme
Preparation of Alkyl Boronic Esters Using Radical-Polar Crossover Reactions of Vinylboron Ate Complexes
Marvin Kischkewitz and Armido Studer
Org. Synth. 2018, 95, 205
DOI: 10.15227/orgsyn.095.0205
Checked by: Helene Wolleb and Erick M. Carreira

Reaction scheme
Preparation of N-(1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ylidene)nitramide
Emerson Teixeira da Silva, Adriana Marques Moraes, Adriele da Silva Araújo, and Marcus Vinícius Nora de Souza
Org. Synth. 2018, 95, 192
DOI: 10.15227/orgsyn.095.0192
Checked by: Philipp C. Roosen, Christopher J. Borths, and Margaret M. Faul

Reaction scheme
Syntheses of Substituted 2-Cyano-benzothiazoles
Hendryk Würfel and Dörthe Jakobi
Org. Synth. 2018, 95, 177
DOI: 10.15227/orgsyn.095.0177
Checked by: Caitlin Lacker, Travis J. DeLano, and Sarah Reisman

Reaction scheme
Preparation of (S)-N-Boc-5-oxaproline
Claudia E. Murar, Thibault J. Harmand, Hikaru Takano, and Jeffrey W. Bode
Org. Synth. 2018, 95, 157
DOI: 10.15227/orgsyn.095.0157
Checked by: Jacob C. Timmerman, Yu-Wen Huang, and John L. Wood

Reaction scheme
Enantioselective Synthesis of (S)-Ethyl 2-((tert-butoxycarbonyl)((tert-butyldimethylsilyl)oxy)amino)-4-oxobutanoate
Thibault J. Harmand, Claudia E. Murar, Hikaru Takano, and Jeffrey W. Bode
Org. Synth. 2018, 95, 142
DOI: 10.15227/orgsyn.095.0142
Checked by: Jacob C. Timmerman, Yu-Wen Huang, and John L. Wood

Reaction scheme
Preparation of Solid Organozinc Pivalates and Their Reaction in Pd-Catalyzed Cross-Couplings
Mario Ellwart, Yi-Hung Chen, Carl Phillip Tüllmann, Vladimir Malakhov, and Paul Knochel
Org. Synth. 2018, 95, 127
DOI: 10.15227/orgsyn.095.0127
Checked by: Kelsey E. Poremba and Sarah E. Reisman

Reaction scheme
Synthesis of N-Acyl Pyridinium-N-Aminides and Their Conversion to 4-Aminooxazoles via a Gold-Catalyzed Formal (3+2)-Dipolar Cycloaddition
Matthew P. Ball-Jones and Paul W. Davies
Org. Synth. 2018, 95, 112
DOI: 10.15227/orgsyn.095.0112
Checked by: Manuela Brütsch, Estíbaliz Merino and Cristina

Reaction scheme
Preparation of 6H-Benzo[c]chromen-6-one
Yang Wang, Yi Shi, and Vladimir Gevorgyan
Org. Synth. 2018, 95, 97
DOI: 10.15227/orgsyn.095.0097
Checked by: Evan R. Darzi and Neil K. Garg

Reaction scheme
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
Richard Y. Liu and Stephen L. Buchwald
Org. Synth. 2018, 95, 80
DOI: 10.15227/orgsyn.095.0080
Checked by: Aurapat (Fa) Ngamnithiporn, Gerit Pototschnig, and Brian M. Stoltz

Reaction scheme
Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles
Kyle M. Lambert, Sherif A. Eldirany, James M. Bobbitt, and William F. Bailey
Org. Synth. 2018, 95, 60
DOI: 10.15227/orgsyn.095.0060
Checked by: Thomas R. DeVino, Andreas R. Rötheli, and Margaret Faul

Reaction scheme
Preparation of Cyclopent-2-enone Derivatives via the Aza-Piancatelli Rearrangement
Meghan F. Nichol, Luis Limon, and Javier Read de Alaniz
Org. Synth. 2018, 95, 46
DOI: 10.15227/orgsyn.095.0046
Checked by: Feng Peng and Kevin Campos

Reaction scheme
Preparation of Fac-Tris(2-Phenylpyridinato) Iridium(III)
Kip A. Teegardin and Jimmie D. Weaver
Org. Synth. 2018, 95, 29
DOI: 10.15227/orgsyn.095.0029
Checked by: Hao Wu, Alexander Sienkiewicz, and Chris Senanayake

Reaction scheme
An Au/Zn-catalyzed Synthesis of N-protected Indole via Annulation of N-arylhydroxamic Acid and Alkyne
Xinpeng Cheng, Yanzhao Wang, and Liming Zhang
Org. Synth. 2018, 95, 15
DOI: 10.15227/orgsyn.095.0015
Checked by: Lucas Morrill, Junyong Kim, and Neil K. Garg

Reaction scheme
Copper and Secondary Amine-Catalyzed Pyridine Synthesis from O-Acetyl Oximes and α,β-Unsaturated Aldehydes
Wei Wen Tan, Bin Wu, Ye Wei, and Naohiko Yoshikai
Org. Synth. 2018, 95, 1
DOI: 10.15227/orgsyn.095.0001
Checked by: Suttipol Radomkit and Chris H. Senanayake

Reaction scheme

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All procedures and characterization data in OrgSyn are peer-reviewed and checked for reproducibility in the laboratory of a member of the Board of Editors