European Journal of Organic Chemistry

Cover image for Vol. 2016 Issue 27

Editor: Haymo Ross, Deputy Editor: Anne Nijs

Impact Factor: 3.068

ISI Journal Citation Reports © Ranking: 2015: 17/59 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry

Microreviews

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Markus Neumeyer, Reinhard Brückner
Nonracemic γ-Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ-Unsaturated Carboxylic Esters

Nonracemic γ‐Lactones from the Sharpless Asymmetric Dihydroxylation of β,γ‐Unsaturated Carboxylic Esters

Over 70 asymmetric Sharpless dihydroxylations of β,γ-unsaturated esters furnishing β-hydroxy-γ-lactones are reviewed. Methodological studies are covered as well as synthetic applications, particularly in natural product synthesis.

Eur. J. Org. Chem. 10.1002/ejoc.201600520

Haibo Mei, Chen Xie, Jianlin Han, Vadim A. Soloshonok
N-tert-Butylsulfinyl-3,3,3-trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl-Containing Amines and Amino Acids of Pharmaceutical Importance

N‐tert‐Butylsulfinyl‐3,3,3‐trifluoroacetaldimine: Versatile Reagent for Asymmetric Synthesis of Trifluoromethyl‐Containing Amines and Amino Acids of Pharmaceutical Importance

Methods for the preparation of compounds containing trifluoromethyl groups are in high demand in the chemical industry. Recently the chemistry of N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine has undergone particular development. Currently it is widely used as a versatile reagent for asymmetric synthesis of trifluoromethyl-containing amines and amino acids with pharmaceutical potential.

Eur. J. Org. Chem. 10.1002/ejoc.201600578

Qian Zhao, Hussein Abou-Hamdan, Laurent Désaubry
Recent Advances in the Synthesis of Flavaglines, a Family of Potent Bioactive Natural Compounds Originating from Traditional Chinese Medicine

Recent Advances in the Synthesis of Flavaglines, a Family of Potent Bioactive Natural Compounds Originating from Traditional Chinese Medicine

With their fascinating pharmacological profiles and complex molecular architectures, the flavaglines have provided a fertile playing field for synthetic organic chemists. This microreview highlights the achievements in the total synthesis of these complex natural products.

Eur. J. Org. Chem. 10.1002/ejoc.201600437

Xiaohua Li, Jianglong Zhu
Glycosylation via Transition-Metal Catalysis: Challenges and Opportunities

Glycosylation via Transition‐Metal Catalysis: Challenges and Opportunities

Development of efficient, mild, and easily operable stereoselective glycosylations is of critical importance to access sufficient amounts of pure and structurally well-defined carbohydrates for studies of their biological functions. Such studies will facilitate our understanding of the role of complex oligosaccharides and glycoconjugates in biological processes as well as the development of carbohydrate-based effective therapeutic agents. This review highlights recent advances in the transition metal catalyzed stereoselective glycosylations for the synthesis of a variety of structurally complex and biologically significant O-, N-, C-, and S-glycosides.

Eur. J. Org. Chem. 10.1002/ejoc.201600484

Carine Maaliki, Emilie Thiery, Jérôme Thibonnet
Emergence of Copper-Mediated Formation of C–C Bonds

Emergence of Copper‐Mediated Formation of C–C Bonds

An overview of copper-catalyzed C–C bond reactions through the main recently developed methodologies is presented.

Eur. J. Org. Chem. 10.1002/ejoc.201600540

Rodney A. Fernandes, Pradnya H. Patil, Dipali A. Chaudhari
Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

Dimeric Pyranonaphthoquinones: Isolation, Bioactivity, and Synthetic Approaches

The dimeric pyranonaphthoquinones, “bis versions” of the naphtho[2,3-c]pyran-5,10-dione moiety, comprises a group of antibiotics that have been isolated from a variety of sources including plants, bacteria, fungi, and insects. This review discusses the naturally occurring dimeric pyranonaphthoquinones, their isolation and bioactivity, and synthetic approaches toward them.

Eur. J. Org. Chem. 10.1002/ejoc.201600544

Jérémy Merad, Jean-Marc Pons, Olivier Chuzel, Cyril Bressy
Enantioselective Catalysis by Chiral Isothioureas

Enantioselective Catalysis by Chiral Isothioureas

Molecular Swiss Army Knives! This review covers the reactivity of chiral isothioureas, which emerged as nucleophilic organocatalysts in 2006. Multiple modes of activation rapidly came to be displayed by these heterocycles; this now makes them powerful catalysts in the toolbox of the organic chemist.

Eur. J. Org. Chem. 10.1002/ejoc.201600399

Harald Gröger
Shibasaki Catalysts and Their Use for Asymmetric Synthetic Applications by the Chemical Industry

Shibasaki Catalysts and Their Use for Asymmetric Synthetic Applications by the Chemical Industry

Shibasaki catalysts are a unique, highly efficient, and broadly applicable class of catalysts for use in asymmetric synthesis. It is these catalytic properties that make them attractive for industrial applications, and companies such as Actelion Pharmaceuticals, Nissan Chemicals, Hokko Chemicals, SKW Trostberg, and Sumitomo Dainippon Pharma jointly with Sunovion Pharmaceuticals have been involved in activities for their commercial use.

Eur. J. Org. Chem. 10.1002/ejoc.201600174

Jonathan R. Carney, Barry. R. Dillon, Stephen P. Thomas
Recent Advances of Manganese Catalysis for Organic Synthesis

Recent Advances of Manganese Catalysis for Organic Synthesis

The manganese-catalysed functionalisation of organic molecules is reviewed with regard to synthetic applications. Manganese-catalysed C–H oxidations, halogenations, cross-couplings and C–H activations are discussed with mechanisms details.

Eur. J. Org. Chem. 10.1002/ejoc.201600018

Aanchal Batra, Paramjit Singh, Kamal Nain Singh
Cross Dehydrogenative Coupling (CDC) Reactions of N,N-Disubstituted Formamides, Benzaldehydes and Cycloalkanes

Cross Dehydrogenative Coupling (CDC) Reactions of N,N‐Disubstituted Formamides, Benzaldehydes and Cycloalkanes

Cross dehydrogenative coupling reactions for carbon–carbon and carbon-heteroatom bond formation have experienced significant progress with substrates such as formamides, benzaldehydes and cycloalkanes. This microreview summarizes such bond formation reactions in substrates that variously are not arylated (e.g., DMF), do not contain a heteroatom (benzaldehydes) or both (cycloalkanes).

Eur. J. Org. Chem. 10.1002/ejoc.201600401

Pier Paolo Giovannini, Olga Bortolini, Alessandro Massi
Thiamine-Diphosphate-Dependent Enzymes as Catalytic Tools for the Asymmetric Benzoin-Type Reaction

Thiamine‐Diphosphate‐Dependent Enzymes as Catalytic Tools for the Asymmetric Benzoin‐Type Reaction

Thiamine-diphosphate-dependent (ThDP-dependent) enzymes are very efficient catalysts for asymmetric benzoin-type condensation. Through chemo- and stereoselective coupling of various carbonyl reagents promoted by enzymes of this family a wide variety of optically active α-hydroxy ketones have been produced. An overview of these synthetically relevant enzymatic benzoin-type reactions is given.

Eur. J. Org. Chem. 10.1002/ejoc.201600228

Jekaterina Bolsakova, Aigars Jirgensons
Synthesis of α-Ethynyl Glycines

Synthesis of α‐Ethynyl Glycines

This microreview gives an overview of the methods published from 1996 to 2015 for the syntheses of ethynyl glycines and synthetically equivalent ethynyl glycinols in racemic and enantioenriched form. These derivatives can serve as versatile building blocks for the preparation of biologically active compounds, including natural products.

Eur. J. Org. Chem. 10.1002/ejoc.201600253

Pradipta Das, Jon T. Njardarson
Anionic Cascade Routes to Sulfur and Nitrogen Heterocycles Originating from Thio- and Aminophosphate Precursors

Anionic Cascade Routes to Sulfur and Nitrogen Heterocycles Originating from Thio‐ and Aminophosphate Precursors

In this microreview article we report the synthesis of sulfur and nitrogen heterocycles via anionic cascade routes employing a phosphate group migration strategy.

Eur. J. Org. Chem. 10.1002/ejoc.201600312

Ummareddy Venkata Subba Reddy, Madhu Chennapuram, Chigusa Seki, Eunsang Kwon, Yuko Okuyama, Hiroto Nakano
Catalytic Efficiency of Primary β-Amino Alcohols and Their Derivatives in Organocatalysis

Catalytic Efficiency of Primary β‐Amino Alcohols and Their Derivatives in Organocatalysis

This review demonstrates the catalytic efficiency of primary β-amino alcohols and their derivatives in organocatalysis. These simple amino alcohols are inexpensive alternatives to other primary amino organocatalysts, being easy to synthesize and air-stable and offering the potential for introduction of different functional groups and alteration of steric sites.

Eur. J. Org. Chem. 10.1002/ejoc.201600164

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  • Pierre-Antoine Faugeras, Benjamin Boëns, Pierre-Henri Elchinger, François Brouillette, Daniel Montplaisir, Rachida Zerrouki, Romain Lucas
    When Cyclodextrins Meet Click Chemistry
    Eur. J. Org. Chem. 2012, No. 22, 4087–4105

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  • Ilhem Zebiri, Sébastien Balieu, Arnaud Guilleret, Romain Reynaud, Arnaud Haudrechy
    The Chemistry of L-Sorbose
    Eur. J. Org. Chem. 2011, No. 16, 2905–2910

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  • Marcel Kienle, Srinivas Reddy Dubbaka, Katja Brade, Paul Knochel
    Modern Amination Reactions
    Eur. J. Org. Chem. 2007, No. 25, 4166–4176
  • Leendert J. van den Bos, Jeroen D. C. Codée, Remy E. J. N. Litjens, Jasper Dinkelaar, Herman S. Overkleeft, Gijsbert A. van der Marel
    Uronic Acids in Oligosaccharide Synthesis
    Eur. J. Org. Chem. 2007, No. 24, 3963–3976

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  • Murray G. Rosenberg, Udo H. Brinker
    Constrained Carbenes
    Eur. J. Org. Chem. 2006, No. 24, 5423–5440

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  • Brian Halton
    The Fulvalenes
    Eur. J. Org. Chem. 2005, No. 16, 3391–3414

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  • Lev M. Yagupolskii, Svetlana V. Shelyazhenko, Irina I. Maletina, Vitalij N. Petrik, Eduard B. Rusanov, Alexander N. Chernega
    The Aza Curtius Rearrangement
    Eur. J. Org. Chem. 2001, No. 7, 1225–1233

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  • Dmitry M. Rudkevich, Julius Rebek, Jr.
    Deepening Cavitands
    Eur. J. Org. Chem. 1999, No. 9, 1991–2005

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