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 Harder 3D-printed tools – Researchers from Dresden introduce new process for hardmetal industry
11.10.2018 | Fraunhofer-Institut für Keramische Technologien und Systeme IKTS

nachricht Flying High with VCSEL Heating
04.10.2018 | 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: UNH scientists help provide first-ever views of elusive energy explosion

Researchers at the University of New Hampshire have captured a difficult-to-view singular event involving "magnetic reconnection"--the process by which sparse particles and energy around Earth collide producing a quick but mighty explosion--in the Earth's magnetotail, the magnetic environment that trails behind the planet.

Magnetic reconnection has remained a bit of a mystery to scientists. They know it exists and have documented the effects that the energy explosions can...

Im Focus: A Chip with Blood Vessels

Biochips have been developed at TU Wien (Vienna), on which tissue can be produced and examined. This allows supplying the tissue with different substances in a very controlled way.

Cultivating human cells in the Petri dish is not a big challenge today. Producing artificial tissue, however, permeated by fine blood vessels, is a much more...

Im Focus: A Leap Into Quantum Technology

Faster and secure data communication: This is the goal of a new joint project involving physicists from the University of Würzburg. The German Federal Ministry of Education and Research funds the project with 14.8 million euro.

In our digital world data security and secure communication are becoming more and more important. Quantum communication is a promising approach to achieve...

Im Focus: Research icebreaker Polarstern begins the Antarctic season

What does it look like below the ice shelf of the calved massive iceberg A68?

On Saturday, 10 November 2018, the research icebreaker Polarstern will leave its homeport of Bremerhaven, bound for Cape Town, South Africa.

Im Focus: Penn engineers develop ultrathin, ultralight 'nanocardboard'

When choosing materials to make something, trade-offs need to be made between a host of properties, such as thickness, stiffness and weight. Depending on the application in question, finding just the right balance is the difference between success and failure

Now, a team of Penn Engineers has demonstrated a new material they call "nanocardboard," an ultrathin equivalent of corrugated paper cardboard. A square...

All Focus news of the innovation-report >>>

Anzeige

Anzeige

VideoLinks
Industry & Economy
Event News

Optical Coherence Tomography: German-Japanese Research Alliance hosted Medical Imaging Conference

19.11.2018 | Event News

“3rd Conference on Laser Polishing – LaP 2018” Attracts International Experts and Users

09.11.2018 | Event News

On the brain’s ability to find the right direction

06.11.2018 | Event News

 
Latest News

New materials: Growing polymer pelts

19.11.2018 | Materials Sciences

Earthquake researchers finalists for supercomputing prize

19.11.2018 | Information Technology

Controlling organ growth with light

19.11.2018 | Life Sciences

VideoLinks
Science & Research
Overview of more VideoLinks >>>