Marcus Angelin

Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process.

Crystallization-induced secondary selection from a tandem driven dynamic combinatorial library is presented. In a one-pot experiment, an initial nitroaldol equilibrium was kinetically driven by a tandem reaction resulting in a subsequent dynamic library of diastereoisomers. This library was then further driven by a phase change, resulting in amplification and isolation of a highly diastereomerically enriched and synthetically interesting isoindolinone.

Tandem driven dynamic combinatorial resolution via Henry-iminolactone rearrangement

An unexplored type of tandem reaction is used to kinetically resolve a dynamic combinatorial library resulting in quantitative amplification of an interesting 3-substituted isoindolinone,

Diastereoselective One-Pot Tandem Synthesis of 3-Substituted Isoindolinones: A Mechanistic Investigation.

The mechanism of a base-catalyzed one-pot reaction of 2-cyanobenzaldehyde and primary nitroalkanes, to produce 3-substituted isoindolinones, has been investigated. A route starting with a nitroaldol (Henry) reaction, followed by a subsequent cyclization and rearrangement, was supported by intermediate analogue synthesis and DFT calculations. Direct diastereoselective crystallization from the reaction mixture was also achieved and studied for a number of substrates. Furthermore, the 3-substituted isoindolinones are an interesting group of compounds, both present important natural products, as well as being precursors to other valuable building blocks.

Tandem driven dynamic self-inhibition of acetylcholinesterase

A concept of tandem driven dynamic self-inhibition is demonstrated through dynamic inhibitors of acetylcholinesterase (AChE) using reversible transthiolesterification.

Making a Chemical Rainbow

In this laboratory experiment, high school students are challenged to prepare a six-layered chemical “rainbow” in a test tube. Students start with six unknown, colorless liquids and six pigments ranging from violet to red. The experiment is problem based and forces the students to apply their knowledge of solubility and density and combine it with creative and critical thinking to come up with a successful strategy to make the rainbow. This is followed by experimental testing to find the unique solution. Finally, coloring and correct layering of the liquids produces the final and aesthetically pleasing result, a chemical rainbow.