Previous work in this research group had resulted in the synthesis of an aziridine intermediate from o-bromobenzaldehyde by way of imine formation and subsequent reduction with sodium borohydride. Creation of a nucleophilic carbon at the adjacent sp2 arene carbon using bromine-lithium exchange should result in expansion of the three-membered aziridine ring, resulting in tetrahydroisoquinoline, a backbone for several natural products. This semester's research focuses on the duplication of previous work, as well as improving the efficiency of the aziridine formation process. Future work toward developing suitable conditions and reagents to effect ring-opening of the aziridine to create the desired tetrahydroisoquinoline will be reported in due course.
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Back to The 37th Middle Atlantic Regional Meeting (May 22-25, 2005)