Asymmetric Amination of meso-Epoxide with Vegetable Powder as a Low-Toxicity Catalyst.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Yuki TakeuchiHiroyuki Kurata

Abstract

This paper describes the scope and limitation of substrates subjected to asymmetric amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening commercially available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals.

References

Jul 5, 2003·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·T TakahashiS A Ruckman
Aug 12, 2005·Organic Letters·Najmodin Azizi, Mohammad R Saidi
Dec 7, 2007·Accounts of Chemical Research·Franz Dietrich Klingler
May 20, 2008·Current Opinion in Plant Biology·Debra Mohnen

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