Case Studies

Enantioconvergent Cross-Coupling of Racemic Secondary Organozinc Reagents

"Among a range of topics, we work on asymmetric palladium catalysis for deracemization reactions. Over the last few years we have become particularly interested in the use of chiral racemic secondary organozinc compounds for such transformations. These compounds show remarkable functional group tolerance compared to other classes of organometallic reagents, such as organolithium or Grignard reagents. However, the high degree of covalency of the carbon–zinc bond and the resulting slower rate of racemization compared to the more ionic organolithium or Grignard reagents constitutes a major challenge for deracemization reactions (see Scheme 1). To overcome this hurdle and find  a suitable catalyst system, a solid knowledge of the background literature is essential. I therefore regularly consult Science of Synthesis Online as a comprehensive source of information and enormously value the high quality of the individual articles accessible with just a few mouse clicks."

Alexander Preinfalk, Institute of Organic Chemistry, University of Vienna

 

Direct C(sp3)-H Amination for Pyrrolidine Synthesis

"Our research group is focused on the development of catalytic processes for new amination reactions. In particular, we are interested in the Hofmann–Löffler reaction in which valuable pyrrolidines are the final products. In this case study, we gathered information with the assistance of Science of Synthesis Online about pyrrolidine’s usefulness and plausible routes toward its synthesis through direct C(sp3)-H amination. For the latter, various sections were found to be the most adequate to sum-up all the different processes. The structure tool was used for the searches to afford the results presented here."

Thomas Duhamel, Institute of Chemical Research of Catalonia (ICIQ), Tarragona, Spain

 

Identifying Suitable Strategies for Silole Synthesis

“We are currently working in the field of group 4 metalloles with a main focus on siloles. Siloles are higher congeners of cyclopentadiene, which have an astoundingly narrow HOMO–LUMO gap. For this reason, we are interested in their electronic properties and their use as ligands for early transition and rare earth metals. In this case study I utilize Science of Synthesis Online to search the literature for strategies toward silole synthesis and to reduce the various options to a small number of most suitable pathways.”

Alexander Pöcheim, Graz University of Technology, Institute of Inorganic Chemistry, Austria

 

Synthesis of Functionalized Iodoarenes by Iododecarboxylation of Aromatic Carboxylic Acids

Fateh Veer Singh "Our research group is currently involved in the synthesis of new hypervalent iodine reagents and their applications in organic synthesis. These reagents have received particular attention due to their oxidation properties, mild reaction conditions, and environmentally friendly nature. Generally, hypervalent iodine reagents exist in the form of iodine(III) and iodine(V) reagents. In our on-going research project, we are aiming to synthesize novel iodine(III) reagents 2 by the oxidation of iodoarenes 1 (Scheme 1). In order to synthesize the iodoarenes, Science of Synthesis Online was used as a tool for literature search. Performing a literature search using this tool, we were able to find an excellent method for the synthesis of iodoarenes. "

Fateh Veer Singh, VIT University, Chennai Campus, Chennai, India

 

Synthetic Approaches to Porphyrins by (2 + 2) Routes

 Zhang Zongyao "In this case study, synthetic approaches toward porphyrins were investigated using Science of Synthesis Online. The search provided us with common synthetic pathways as well as credible remarks. The various bond-forming strategies presented were of great help."

Zhang Zongyao, Renmin University of China, Beijing, China

 

[ 2 + 2 + 2 ] Cyclotrimerization of Alkynes and Nitriles

Gabriela Siemiaszko "We are interested in [2 + 2 + 2] cyclotrimerizations of alkynes for the preparation of variously substituted benzene rings. Science of Synthesis Online was used to undertake a comprehensive review of this topic."

Gabriela Siemiaszko, Ecole Polytechnique, Palaiseau, France

 

Analysis of Synthetic Routes toward Allenylsilanes

Valentin Bochatay "In this case study, we investigated possible synthetic approaches toward allenylsilanes (Scheme 1) using Science of Synthesis Online. The survey provided a general and comprehensive picture of the available routes presented in a clear and synthetic way."

Valentin Bochatay, Sorbonne Universités, Paris, France

 

Palladium-Catalyzed Trimethylenemethane (TMM) Cycloaddition

Chao Zheng "In this case study, a literature survey on palladium-catalyzed trimethylenemethane (TMM) cycloaddition reactions was conducted with Science of Synthesis Online."

Chao Zheng, Shanghai Institute of Organic Chemistry, China 

 

Cyclopropanation of Unactivated Alkenes

"Science of Synthesis Online is a very useful tool for every synthetic chemist and is complementary to other reaction databases. It also provides a short full text introduction with several relevant examples from the literature for a specific transformation. In some cases an experimental procedure is also included which can be very time-saving."

Aleksandar Stojanovic, Novartis Institutes for Biomedical Research, Basel

 

Synthesis of α-Oxoaldehyde Hydrates by the Oxidation of Diazo Compounds Using Dimethyldioxirane

"Thieme’s Science of Synthesis Online was used to find possible synthetic routes to α-oxoaldehyde hydrates. The structure-based search was very useful to reach the article we wanted, and the content of the article was informative and concise. Thus, Science of Synthesis Online was found to be an excellent tool to find possible synthetic routes to the compounds of interest."

Akinobu Matsuzawa, Hoshi University, Tokyo

 

Asymmetric [1,2]-Wittig Rearrangement and Synthesis of Fused Heteroaromatics

"Science of Synthesis Online has been used to identify methods of performing asymmetric [1,2]-Wittig rearrangement reactions. Procedures for the synthesis of benzyl ethers and O-aryl carbamates allowed suitable [1,2]-Wittig rearrangement precursors to be prepared and the chapter on benzo[b]furans provided a comprehensive overview of their Synthesis."

Andrew Harper, University of St Andrews

 

Analysis of Synthetic Approaches toward Glyoxylic Acids

"In this case study, we investigated possible synthetic approaches toward glyoxylic acids with Science of Synthesis Online. The search was based on Section 20.2.5 (2-Oxo- and 2-Imino-Substituted Alkanoic Acids) and the structure-based query tool. The results of both approaches will be discussed and compared."

Franziska Merkt (left) and Charlotte Gers (right), Heinrich-Heine-Universität, Düsseldorf

 

Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides on Sulfur Compounds

"Our research work focuses on the development of a library of novel antibacterial compounds with tetramates as the core scaff old, accessed via a Dieckmann ring closure on a substituted thiazolidine ring. By adding diversity around this tetramate core, we can rapidly generate a library of tetramates which are then assayed for biological potency."

Tharindi Panduwawala, University of Oxford (Moloney Group)

 

Identification of Synthetic Approaches to Heteroatom-Substituted Phosphine Ligands

"The Science of Synthesis database search has been used to identify possible synthetic approaches to a relatively broad ligand library of phosphine ligands bearing heteroatoms in the carbon backbone. In particular, the structure-based query was found to be a useful tool to quickly identify various synthetic
approaches for the compounds of interest.
"

Johannes Teichert, TU Berlin

 

Coupling and Deprotection Methods in Solution-Phase Peptide Synthesis

"The ease of access, intuitive search function and quality of content makes Thieme Chemistry’s Science of Synthesis among the best online research tools out there for synthetic chemists. This case study looks specifically at the use of the Science of Synthesis to locate protocols for the various coupling and deprotection reactions used extensively in solution-phase peptide synthesis."

Stefan Lawrenson, University of York (North Group)

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