Alkenes as chiral building blocks
Chiral technologies are increasingly important in the pharmaceutical and fine chemical industries. Single enantiomer chemicals and drugs are of huge interest, often showing increased efficacy and a decrease in harmful side effects.
This technology offers a flexible new method for creating chiral centres from low-cost starting materials.
Chirality – important in nature
Many industrially important biologically active molecules are chiral, lacking an internal plane of symmetry, and difficult to synthesise. The invention of asymmetric catalytic synthesis is therefore one of chemistry’s great achievements. Many broadly useful methods for catalytic asymmetric oxidation and reduction now exist. However, far fewer, simple and efficient catalytic asymmetric methods for forming C-C bonds (present in so many useful compounds) have been invented until now.
Other approaches to asymmetric C-C bond formation
The development of asymmetric C-C bond forming reactions that are new, powerful or practical is of great importance. The use of organometallic reagents means that many chiral targets are now attainable. However, such reagents are expensive, very reactive, air/moisture sensitive and require carrying out the reaction at very low temperatures.
The Oxford invention
With consideration being given to efficiency, waste, and using readily available and convenient to handle materials, Oxford researchers have developed a method that allows alkenes to be used in the same way as organometallic nucleophiles in catalytic asymmetric C-C bond formation.
Reactions may be performed using alkenes as the nucleophile, at room temperature, with a wide variety of solvents and functional groups being tolerated. Terminal alkenes are among the most readily available, inexpensive organic molecules. These provide a tremendous value-added component in converting cheap raw materials into highly functionalized compounds. This new development has application in the industrial synthesis of small molecules.
The technology is the subject of a UK patent application. Companies interested in progressing the commercial opportunities are invited to contact Oxford University Innovation. Request more information if you would like to discuss this further.
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