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.

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 August 28, 2014 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 August 28, 2014).

Share This




More Matter & Energy News

Thursday, August 28, 2014

Featured Research

from universities, journals, and other organizations


Featured Videos

from AP, Reuters, AFP, and other news services

Australian Airlines Relax Phone Ban Too

Australian Airlines Relax Phone Ban Too

Reuters - Business Video Online (Aug. 26, 2014) Qantas and Virgin say passengers can use their smartphones and tablets throughout flights after a regulator relaxed a ban on electronic devices during take-off and landing. As Hayley Platt reports the move comes as the two domestic rivals are expected to post annual net losses later this week. Video provided by Reuters
Powered by NewsLook.com
Hurricane Marie Brings Big Waves to California Coast

Hurricane Marie Brings Big Waves to California Coast

Reuters - US Online Video (Aug. 26, 2014) Huge waves generated by Hurricane Marie hit the Southern California coast. Rough Cut (no reporter narration). Video provided by Reuters
Powered by NewsLook.com
Chinese Researchers Might Be Creating Supersonic Submarine

Chinese Researchers Might Be Creating Supersonic Submarine

Newsy (Aug. 26, 2014) Chinese researchers have expanded on Cold War-era tech and are closer to building a submarine that could reach the speed of sound. Video provided by Newsy
Powered by NewsLook.com
Breakingviews: India Coal Strained by Supreme Court Ruling

Breakingviews: India Coal Strained by Supreme Court Ruling

Reuters - Business Video Online (Aug. 26, 2014) An acute coal shortage is likely to be aggravated as India's supreme court declared government coal allocations illegal, says Breakingviews' Peter Thal Larsen. Video provided by Reuters
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:
from the past week

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