Featured Research

from universities, journals, and other organizations

Broadening the scope for synthesizing optically active compounds

Date:
May 9, 2014
Source:
Organization of Frontier Science and Innovation, Kanazawa University
Summary:
Chiral compounds are increasingly important in chemical manufacturing. They are distinguished by a special kind of asymmetry in their molecular structure. Scientists have now developed a method for desymmetrizing compounds to produce new chiral molecules. The process allows 99% selectivity in the chemicals produced.

Credit: Image courtesy of Organization of Frontier Science and Innovation, Kanazawa University

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

Related Articles


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.

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."


Story Source:

The above story is based on materials provided by Organization of Frontier Science and Innovation, Kanazawa University. Note: Materials may be edited for content and length.


Journal Reference:

  1. Mari Yoshida, Naotaro Sassa, Tomomitsu Kato, Shuhei Fujinami, Takahiro Soeta, Katsuhiko Inomata, Yutaka Ukaji. Desymmetrization of 1,4-Pentadien-3-ol by the Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines. Chemistry - A European Journal, 2014; 20 (7): 2058 DOI: 10.1002/chem.201302889

Cite This Page:

Organization of Frontier Science and Innovation, Kanazawa University. "Broadening the scope for synthesizing optically active compounds." ScienceDaily. ScienceDaily, 9 May 2014. <www.sciencedaily.com/releases/2014/05/140509131559.htm>.
Organization of Frontier Science and Innovation, Kanazawa University. (2014, May 9). Broadening the scope for synthesizing optically active compounds. ScienceDaily. Retrieved January 25, 2015 from www.sciencedaily.com/releases/2014/05/140509131559.htm
Organization of Frontier Science and Innovation, Kanazawa University. "Broadening the scope for synthesizing optically active compounds." ScienceDaily. www.sciencedaily.com/releases/2014/05/140509131559.htm (accessed January 25, 2015).

Share This


More From ScienceDaily



More Matter & Energy News

Sunday, January 25, 2015

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Obama Reveals Nuclear Breakthrough on Landmark India Trip

Obama Reveals Nuclear Breakthrough on Landmark India Trip

Reuters - News Video Online (Jan. 25, 2015) In a glow of bonhomie, U.S. President Barack Obama and Indian Prime Minister Narendra Modi unveil a deal aimed at unlocking billions of dollars in nuclear trade. Pavithra George reports. Video provided by Reuters
Powered by NewsLook.com
NTSB: Missing Planes' Black Boxes Should Transmit Wirelessly

NTSB: Missing Planes' Black Boxes Should Transmit Wirelessly

Newsy (Jan. 23, 2015) In light of high-profile plane disappearances in the past year, the NTSB has called for changes to make finding missing aircraft easier. Video provided by Newsy
Powered by NewsLook.com
Iconic Metal Toy Meccano Goes Robotic

Iconic Metal Toy Meccano Goes Robotic

Reuters - Innovations Video Online (Jan. 22, 2015) Classic children&apos;s toy Meccano has gone digital, releasing a programmable kit robot that can be controlled by voice recognition. The toymakers say Meccanoid G15 KS is easy to use and is compatible with existing Meccano pieces. Jim Drury reports. Video provided by Reuters
Powered by NewsLook.com
The VueXL From VX1 Immersive Smartphone Headset!

The VueXL From VX1 Immersive Smartphone Headset!

Rumble (Jan. 22, 2015) The VueXL from VX1 is a product that you install your smartphone in and with the magic of magnification lenses, enlarges your smartphones screen so that it&apos;s like looking at a big screen TV. Check it out! Video provided by Rumble
Powered by NewsLook.com

Search ScienceDaily

Number of stories in archives: 140,361

Find with keyword(s):
Enter a keyword or phrase to search ScienceDaily for related topics and research stories.

Save/Print:
Share:

Breaking News:

Strange & Offbeat Stories


Space & Time

Matter & Energy

Computers & Math

In Other News

... from NewsDaily.com

Science News

Health News

Environment News

Technology News



Save/Print:
Share:

Free Subscriptions


Get the latest science news with ScienceDaily's free email newsletters, updated daily and weekly. Or view hourly updated newsfeeds in your RSS reader:

Get Social & Mobile


Keep up to date with the latest news from ScienceDaily via social networks and mobile apps:

Have Feedback?


Tell us what you think of ScienceDaily -- we welcome both positive and negative comments. Have any problems using the site? Questions?
Mobile: iPhone Android Web
Follow: Facebook Twitter Google+
Subscribe: RSS Feeds Email Newsletters
Latest Headlines Health & Medicine Mind & Brain Space & Time Matter & Energy Computers & Math Plants & Animals Earth & Climate Fossils & Ruins