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73 matches found for cycloadditions

Cycloaddition Reagents

Aldrich ChemFiles 2006, 6.2, 8. 1-(2-Methoxyethoxy)-1-vinycyclopropane Vinylcyclopropanes (VCPs) are excellent scaffolds for construction of seven-membered and bicyclic ring systems. Paul Wender, of Stanford University, has developed a simple but versatile VCP reagent (1-(2-methoxyethoxy)-1-vinycycl...

Cycloaddition

Aldrich ChemFiles 2009, 9.5, 7. Following their work developing chiral gold complexes for the enantioselective hydroamination, Toste and coworkers looked at the [2+2] cycloaddition of allenenes.1 Resulting from this work was the first catalyzed cycloisomerization of allenenes to alkylidenes-cyclobut...

Alkyne Hydrosilylation

• • Download PDF • Vinyl-metal reagents play a pivotal role in organic synthesis. Among the vinyl-metal reagents available, silicon-based reagents are of increasing importance. This is largely due to their low cost, minimal toxicity, ease of handling, and the simplicity of byproduct removal. Particu...

Click Chemistry, a newer approach to the synthesis of drug-like molecules

A "Click" Away from Discovery The traditional process of drug discovery based on natural secondary metabolites has often been slow, costly, and labor-intensive. Even with the advent of combinatorial chemistry and high-throughput screening in the past two decades, the generation of leads is dependent...

Cycloisomerization of 1,4-, 1,5-,1,6-, and 1,7-Enynes

Aldrich ChemFiles 2009, 9.5, 4. The enyne cycloisomerization is one of the most important reaction for the synthesis of functionalized cyclic structures.1 The structural complexity resulting from the cyclization of relatively simple acyclic subunits explains the enthusiasm surrounding this method. A...

Janis Louie Group – Professor Product Portal

Professor Product Portal Index Professor Janis Louie Professor Louie's research focuses on the discovery and mechanistic understanding of new reactions catalyzed by transition metal complexes. She has developed a highly active Ni(0) catalyst that effectively mediates a variety of cycloaddition and i...

Alkynes

Aldrich ChemFiles 2006, 6.6, 6. Alkynes have been used for many years in the Sonogashira coupling reaction1 and related Castro-Stephens reaction,2 and have recently gained considerable interest in the Huisgen 1,3- dipolar cycloaddition with organic azides.3 Recently, Walsh demonstrated the use of te...

Intramolecular Cycloaddition of 1,3-Enynes with Alkenes | ChemFiles Volume 10 Article 4

Echavarren and co-workers employed a crystalline gold complex containing either the o-biphenyl phosphine ligand JohnPhos, or a bulky aryl ether phosphine under mild conditions to eff ect the [4+2] cycloaddition of 1,3-enynes with olefi ns. A family of biand tricyclic scaff olds were prepared in good...

Polyethylene Glycol Building Blocks for PEGylation

Related Links • PEG Selection Guide • • Download PDF • Circulatory half-life is a key success factor for new drugs. In this respect, modification of potential candidates ranging from non-peptidic small molecules to peptides and proteins, antibody fragments, aptamers, and saccharides or oligonucleoti...

Photocatalysis

Visible light photoredox catalysis has emerged as a powerful tool in organic synthesis, building upon the foundation set by early pioneers in the areas of radical chemistry and photochemistry. Photoredox chemistry allows one to forge new bonds via open shell pathways and facilitates the rapid assemb...

Intermolecular [4+3]-Annulation

Aldrich ChemFiles 2009, 9.5, 4. In 2008, Toste and coworkers developed a new method to synthesize azepines using a Au(III) catalyst.1 Following the work done by the group with sulfoxides showing that the allylgold intermediate can be induced to react as a nucleophile, Shapiro and Toste reacted vario...

Asymmetric Cycloaddition

The asymmetric 1,3-dipolar cycloaddition reaction is of the utmost importance for the enantioselective synthesis of five-membered heterocycles. Cabrera et al. introduced a new family of ligands consisting of a planar chiral P,S-ligand, named Fesulphos, for the 1,3-dipolar cycloaddition of azomethine...

Chiral Phospholane Ligands

ChemFiles 2007, 7.3, 15. Chiral phospholane ligands have been used extensively in transition metal-catalyzed asymmetric hydrogenations and other novel asymmetric reactions including [4+1] cycloadditions, imine alkylations, and allylborations. Available in either enantiomeric form with Me, Et, and i-...

Conjugated Polymers for the Engineering of Device/Tissue Interface

• • Download PDF • Department of Materials Science and Engineering The University of Delaware Newark, DE 19716 *Email: milty@udel.edu There is considerable interest in the development of conjugated, electronically and ionically active polymers for interfacing active biomedical devices with living ti...

Yoon Group – Professor Product Portal

Professor Product Portal Index Professor Tehshik Yoon One major theme of research in the Yoon lab is the development of unique chemical transformations enabled by visible light photochemistry. A variety of transition metal photocatalysts responsive to visible light are known, and the Yoon lab has sh...

Chemical Ligation by Click Chemistry—A “Click” Away from Discovery

The traditional process of drug discovery based on natural secondary metabolites has often been slow, costly, and laborintensive. Even with the advent of combinatorial chemistry and high-throughput screening in the past two decades, the generation of leads is dependent on the reliability of the indi...

Phosgene Application in Modern Synthesis

Vol. 2, No. 7 Eckert's Cartridges for Safe Phosgenations Introduction / Applications / Phosgene and Substitutes / Instructions for Use / References Applications of Phosgene in Modern Synthesis Transformations Using Phosgene Phosgene is a small bifunctional molecule of high synthetic value. It is use...

DuPhos and BPE Phospholane Ligands

Aldrich ChemFiles 2006, 6.8, 3. Asymmetric hydrogenation reactions represent the ideal process for the commercial manufacture of single-enantiomer compounds, because of the ease by which these robust procedures can be scaled up and because of the low levels of byproducts generated in these asymmetri...

Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents

Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents Enantioselective allylation of aldehydes Practical, enantioselective allylation of acylhydrazones Enantioselective allylation of ketimines: synthesis of tertiary carbinamines Friedel-Crafts Alkylation with Acylhydrazones A...

Nicewicz Photoredox Catalysts for Anti-Markovnikov Alkene Hydrofunctionalization

While Markovnikov alkene reactivity is very well developed and utilized commonly in the synthesis of commodity and research chemicals, catalytic access to the anti-Markovnikov-selective adducts is a much less-developed endeavor. In collaboration with Professor David Nicewicz, Sigma-Aldrich is proud ...

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.1 The absence of exogenous metal catalysts makes these reactions suitable for the in vivo applications of bioorthogonal chemistry ...

Vaulted Biaryl Ligands and BINOL Derivatives

Aldrich ChemFiles 2006, 6.10, 5. BINOL and its derivatives are some of the mostly widely used classes of ligands in asymmetric synthesis, and are utilized in a broad array of reaction classes including: Diels-Alder, ene, carbonyl addition and reductions, Michael additions, as well as many others. Wh...

Azide Building Blocks for Chemical Ligation

Aldrich ChemFiles 2010, 10.2, 6. Dr. Matthias Junkers Dr. Matthias Junkers Product Manager Email: matthias.junkers@sial.com Chemoselective ligation strategies are a key success factor for chemical biology research. Ligation techniques open pathways to fully synthetic large peptides and even proteins...

Poly(2-Oxazoline)S: The Versatile Polymer Platform for Biomedicine

Victor R. de la Rosa,1 An Van Den Bulcke,2 and Richard Hoogenboom1* 1Supramolecular Chemistry Group, Department of Organic and Macromolecular Chemistry Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium 2ChemTech, Department of Organic and Macromolecular Chemistry, Ghent University Krijgslaan ...

Allenes

Versatile building blocks with ability to participate in a diverse array of reactions The past couple of decades have witnessed a surge in the popularity of allenes as viable building blocks for a wide variety of synthetic applications.1 Their versatility allows them to participate in nucleophilic a...

Zhang Group - Professor Product Portal Index

Professor Product Portal Index Professor Liming Zhang The major research thrust in Professor Liming Zhang’s group is homogeneous gold catalysis ranging from discovery of novel reactivities, design of new ligands, development of versatile synthetic methods and application in natural product synthesis...

(R)-(+)- and (S)-(–)-Stericol® New, Effective Chiral Auxiliaries

The introduction of chirality to organic molecules through the use of auxiliaries is a basic strategy in organic chemistry. Chiral benzylic alcohols are of particular interest because they often afford useful levels of stereoselection and are generally easy to cleave. Preparation of Dichlorocyclobut...

OrganoCatalysts

Vol . 2, 2002 Supplement Grubbs' Catalysts & MacMillan's OrganoCatalysts™ Download PDF (641 KB) Grubbs' Catalysts / MacMillan's OrganoCatalysts™ / Verkade's Superbases / Metal Catalysts and Ligands MacMillan's OrganoCatalysts™ The vast majority of useful catalytic transformations involve inorganic o...

Triazolylphenylglyoxal Reagents: Arginine-Directed Bioconjugation

Chemical ligation strategies are widely utilized for the modification of biological macromolecules in biotechnology and medicine and for the development of functional materials. In particular, reagents that can modify the surface of proteins, typically through reactive side chains, have found broad ...

Click Chemistry

Perhaps no reaction in the click family has received more attention than the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes with organoazides to yield 1,4-disubstituted 1,2,3-triazoles (Scheme 1).1 True to a “good” click reaction, the reaction is reliable and high yielding, ea...