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An entry to optically active oxazolidinones: The use of neutral phosphonium salt catalysts

July 12, 2019

Oxazolidinones are coveted in the field of medicine and pharmacology for their bioactive properties. There is hope that structurally different types of oxazolidinones can be building blocks for new drugs. With this research, Assistant Professor Yasunori Toda led a team of researchers at Shinshu University to use a neutral phosphonium salt catalyst for the oxazolidinone synthesis from glycidols and isocyanates. Although the conventional method by basic catalysis caused loss of enantiomeric excess in the reaction using optically pure glycidol, the neutral catalysis inhibited the undesired racemization to afford the product in high yields with high selectivities.

Assistant Professor Toda sat down with us for a brief interview about his research into oxazolidinones.

1) What is the aim of this study?
    The development of neutral catalysts. Now, we are focusing on the catalytic ability of the molecule, which is one of the phosphonium salts, called?tetraarylphosphonium salts.
2) What is the most important message from the paper that you want readers to understand and remember?
    The most important message to remember is that the iodide ion of the catalyst works as a hydrogen-bond acceptor.
3) What was the most challenging part and exciting aspect of the research?
    Making a new and original molecule is a fun part of organic chemistry, but which is always very challenging, because nobody knows how the molecule works.
4) What's the next step?
    We are curious of carbon dioxide fixation. The use of carbon dioxide instead of isocyanates can be interesting. We also need to understand the precise mechanism of the reaction by computational studies.
5) What is your ultimate goal?
    My goal is the development of my name reaction like Toda reaction, which would be my pleasure as a chemist.
With the increase of drug resistant infections, new synthetic approaches to potential drug targets are very welcome. For further information please read the article on Chemical Communications.
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Shinshu University

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