Broadening the Scope for Optically Active Compounds

Creating optically active chiral compounds — which are becoming more and more important in chemical manufacturing — just got a bit easier.

A team from Kanazawa University has devised a method for producing chiral molecules via desymmetrizing compounds. The method allows 99 percent selectivity and could be useful in preparing optically active chemicals that contain nitrogen and oxygen, according to the researchers.

Chiral compounds are optically active in that one stereoisomer rotates the plane of incident polarized light to the left, while the other rotates it to the right. Similar methods already exist but the range of compatible compounds is often limited.

Desymmetrization of the divinyl carbinol was accomplished by the asymmetric 1, 3-dipolar cycloaddition of azomethine imines based on a magnesium-mediated, multinucleating chiral reaction system utilizing diisopropyl (R, R) tartrate as the chiral auxiliary. Courtesy of Kanazawa University.

In their study, the researchers focused on divinyl carbinols, a compound that brings together an ethylene molecular group and an alcohol derived from methanol. Desymmetrization of this compound can provide new optically active alcohol derivatives that contain useful functional groups for further chemical transformations.

The researchers’ new approach expands on previous work in the field, which has demonstrated an asymmetric cycloaddition reaction where compounds with unsaturated double, triple or more bonds combine to form a ring.

The research is published in Chemistry: A European Journal (doi: 10.1002/chem.201302889).

For more information, visit www.kanazawa-u.ac.jp.