Research Interests


Welcome to the world of chiral aziridine chemistry!

Aziridine is the smallest heterocycle containing nitrogen. It has similar ring strain of an epoxide which is a structural “cousin”.  Therefore, we may expect similar chemistries between aziridines and epoxides due to structural similarity.  However, we’ve found there are many differences in terms of reactivity and also structural modification of those heterocyclic systems.

 


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  We borrowed “Lego Block Concept” from the famous children’s toy.  Each of Lego blocks has very simple structural shape.  However, kids can build any kind of 3-dimensional structures some of which are very complex using their creativity and imagination. We anticipated functionalized aziridines can be used as molecular building block (as Lego) for the syntheses of many structurally complex and multi-functionalized biologically active compounds. Therefore, we synthesized 2-functionalized chiral aziridines from readily available starting materials and studied their reactivity toward various organic molecules as well as the transformations of the aziridine ring to a variety of structurally modified multi-functionalized organic compounds. 


Aziridine-2-carboxylates can act as the chiral C-3 starting materials for the syntheses of many structurally modified natural and unnatural amino acids derivatives, alkaloids, and also biologically active compounds.  We use very simple organic reactions for the structural modifications and would like to develop more efficient ways to obtain multi-functionalized molecules which are not easy to make by other synthetic methods. The followings are some examples of ring transformations.

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Our lab is trying to develop new reaction methodologies using chiral aziridines, and welcome you to join the exciting aziridine chemistries! 




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