The research group of Chiba University's Satoshi Wata (2nd year master's student) and Takuya Hashimoto (Chiba Iodine Resources Innovation Center) and others are working on a new organic product that uses iodine, a natural resource that is abundantly produced in Chiba. Succeeded in developing a synthetic method.It can be widely used from drug discovery to basic academic research.
1,2-Amino alcohol is an important molecular skeleton that ranks high in the global sales of small molecule drugs.One of the most rational methods for organic synthesis of this molecule is the aminooxydination of alkenes, which are synthesized based on an inexpensive and easily available substance called alkenes.A method using an osmium catalyst is well-known for this synthetic method, but osmium metal is expensive and toxic, and has not been put into practical use in drug development.
Chiba University opened the Chiba Iodine Resources Innovation Center in 2018.Chiba Prefecture is conducting research and development aimed at the effective utilization of iodine, an important natural resource that accounts for about a quarter of the world's production.
Taking advantage of this knowledge, this research group has been engaged in research to replace osmium with inexpensive and low-toxic iodine.The key to the success of the research is the uniquely developed "N- (fluorosulfonyl) carbamic acid ester", a new reagent that gives nitrogen and oxygen to alkenes.Utilizing the knowledge of organic iodine-catalyzed chemistry, which Japanese research has led the world, we were able to efficiently synthesize only 1,2-aminoalcohol with the desired structure from alkenes by mixing the reagent with the substrate.
As a result, a synthetic method that cannot be put into practical use due to the high toxicity of the catalyst by the conventional technique can be performed by using an inexpensive and low-toxic iodine catalyst.Since it is possible to efficiently obtain the main structures that are widely used in pharmaceutical products, it is expected to be a technology that enables easy and rapid synthesis of drug candidates in future drug discovery research.
Paper information:[Journal of the American Chemical Society] Organoiodine-Catalyzed Enantioselective Intermolecular Oxyamination of Alkenes