Forum for Science, Industry and Business

Sponsored by:     3M 
Search our Site:

 

Broadening the scope for synthesizing optically active compounds

09.05.2014

Yutaka Ukaji and colleagues at Kanazawa University have now developed a method for desymmetrising compounds to produce new chiral molecules. The process allows 99% selectivity in the chemicals produced.

Chiral compounds are increasingly important in chemical manufacturing. They are distinguished by a special kind of asymmetry in their molecular structure. 

Yutaka Ukaji and colleagues at Kanazawa University have now developed a method for desymmetrising compounds to produce new chiral molecules. The process allows 99% selectivity in the chemicals produced. http://www.kanazawa-u.ac.jp/research_bulletin/index.html 

The property of chirality is defined by the existence of distinct mirror image geometric arrangements of the constituent parts of a molecule, known as stereoisomers. Just as your right hand cannot be directly superimposed on the left, if the molecule is chiral the mirror images cannot be directly superimposed. Chiral compounds are often described as optically active as one stereoisomer will rotate the plane of incident polarised light to the left and the other will rotate it to the right.

Desymmetrisation methods to produce chiral compounds exist but the range of compounds amenable to the approach remains limited. Ukaji and his colleagues focused on a type of organic compound known as divinyl carbinols – where the vinyl group describes an ethylene molecular group and the carbinol describes an alcohol derived from methanol. Desymmetrisation of divinyl carbinols can provide new optically active alcohol derivatives that contain useful functional groups for further chemical transformations.

The approach developed by the Kanazawa team built on previous work demonstrating an asymmetric ‘cycloaddition’ reaction where compounds with unsaturated (double, triple etc) bonds combine forming a ring. Their current work demonstrates the reaction on divinyl carbinols with selective production of one mirror image product over the other of over 99%.

They conclude in their report on the work, “This method would be useful for the preparation of optically active nitrogen- and oxygen containing chemicals.”

Further information:
Organization of Frontier Science and Innovation
Kanazawa University
Kakuma, Kanazawa, Ishikawa 920-1192, Japan
E-mail: fsojimu@adm.kanazawa-u.ac.jp
Website: http://www.o-fsi.kanazawa-u.ac.jp/en


About Kanazawa University

Kanazawa University, Japan publishes the May 2014 issue of its online newsletter, Kanazawa University Research Bulletin: http://www.kanazawa-u.ac.jp/research_bulletin/index.html

Kanazawa University Research Bulletin highlights the latest research from one of Japan's leading comprehensive universities with its three colleges and 16 schools offering courses in subjects that include medicine, computer engineering, and humanities.

As the leading comprehensive university on the Sea of Japan coast, Kanazawa University has contributed greatly to higher education and academic research in Japan since it was founded in 1949. The University has three colleges and 16 schools offering courses in subjects that include medicine, computer engineering, and humanities.

The University is located on the coast of the Sea of Japan in Kanazawa—a city rich in history and culture. The city of Kanazawa has cultivated a highly respected intellectual profile since the time of the Kaga fiefdom (1598–1867). Kanazawa University is divided into two main campuses: Kakuma and Takaramachi for its approximately 12,200 students including 500 from overseas.


Kanazawa University website: http://www.kanazawa-u.ac.jp/e/index.html

Associated links

Journal information

Mari Yoshida, Naotaro Sassa, Tomomitsu Kato, Shuhei Fujinami, Takahiro Soeta,
Katsuhiko Inomata, and Yutaka Ukaji*
Desymmetrization of 1,4-pentadien-3-ol by the asymmetric 1,3-
dipolar cycloaddition of azomethine imines. Chem. Eur. J. 20 (2014) 2058–2064.
DOI: 10.1002/chem.201302889

Division of Material Sciences, Graduate School of Natural Science and Technology,
Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

*corresponding author, e-mail address: ukaji@staff.kanazawa-u.ac.jp

Adarsh Sandhu | Research SEA News
Further information:
http://www.kanazawa-u.ac.jp/e/index.html
http://www.researchsea.com

Further reports about: Frontier Kanazawa Organization alcohol asymmetric compounds cycloaddition mirror

More articles from Process Engineering:

nachricht New manufacturing process for SiC power devices opens market to more competition
14.09.2017 | North Carolina State University

nachricht Quick, Precise, but not Cold
17.05.2017 | Fraunhofer-Institut für Lasertechnik ILT

All articles from Process Engineering >>>

The most recent press releases about innovation >>>

Die letzten 5 Focus-News des innovations-reports im Überblick:

Im Focus: Highly precise wiring in the Cerebral Cortex

Our brains house extremely complex neuronal circuits, whose detailed structures are still largely unknown. This is especially true for the so-called cerebral cortex of mammals, where among other things vision, thoughts or spatial orientation are being computed. Here the rules by which nerve cells are connected to each other are only partly understood. A team of scientists around Moritz Helmstaedter at the Frankfiurt Max Planck Institute for Brain Research and Helene Schmidt (Humboldt University in Berlin) have now discovered a surprisingly precise nerve cell connectivity pattern in the part of the cerebral cortex that is responsible for orienting the individual animal or human in space.

The researchers report online in Nature (Schmidt et al., 2017. Axonal synapse sorting in medial entorhinal cortex, DOI: 10.1038/nature24005) that synapses in...

Im Focus: Tiny lasers from a gallery of whispers

New technique promises tunable laser devices

Whispering gallery mode (WGM) resonators are used to make tiny micro-lasers, sensors, switches, routers and other devices. These tiny structures rely on a...

Im Focus: Ultrafast snapshots of relaxing electrons in solids

Using ultrafast flashes of laser and x-ray radiation, scientists at the Max Planck Institute of Quantum Optics (Garching, Germany) took snapshots of the briefest electron motion inside a solid material to date. The electron motion lasted only 750 billionths of the billionth of a second before it fainted, setting a new record of human capability to capture ultrafast processes inside solids!

When x-rays shine onto solid materials or large molecules, an electron is pushed away from its original place near the nucleus of the atom, leaving a hole...

Im Focus: Quantum Sensors Decipher Magnetic Ordering in a New Semiconducting Material

For the first time, physicists have successfully imaged spiral magnetic ordering in a multiferroic material. These materials are considered highly promising candidates for future data storage media. The researchers were able to prove their findings using unique quantum sensors that were developed at Basel University and that can analyze electromagnetic fields on the nanometer scale. The results – obtained by scientists from the University of Basel’s Department of Physics, the Swiss Nanoscience Institute, the University of Montpellier and several laboratories from University Paris-Saclay – were recently published in the journal Nature.

Multiferroics are materials that simultaneously react to electric and magnetic fields. These two properties are rarely found together, and their combined...

Im Focus: Fast, convenient & standardized: New lab innovation for automated tissue engineering & drug

MBM ScienceBridge GmbH successfully negotiated a license agreement between University Medical Center Göttingen (UMG) and the biotech company Tissue Systems Holding GmbH about commercial use of a multi-well tissue plate for automated and reliable tissue engineering & drug testing.

MBM ScienceBridge GmbH successfully negotiated a license agreement between University Medical Center Göttingen (UMG) and the biotech company Tissue Systems...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

Event News

“Lasers in Composites Symposium” in Aachen – from Science to Application

19.09.2017 | Event News

I-ESA 2018 – Call for Papers

12.09.2017 | Event News

EMBO at Basel Life, a new conference on current and emerging life science research

06.09.2017 | Event News

 
Latest News

Comet or asteroid? Hubble discovers that a unique object is a binary

21.09.2017 | Physics and Astronomy

Cnidarians remotely control bacteria

21.09.2017 | Life Sciences

Monitoring the heart's mitochondria to predict cardiac arrest?

21.09.2017 | Health and Medicine

VideoLinks
B2B-VideoLinks
More VideoLinks >>>