Correcting cyclic imino ether structures

Abstract

Cyclic imino ethers are pungent compounds that can be polymerized to make materials that may help smuggle drugs into cells. Researchers at Ghent University had been trying, unsuccessfully, to polymerize one such seven-membered compound, synthesized using a reported procedure, when they noticed it lacked the signature smell. Following their noses, and a close inspection of spectral data, the team discovered that the nearly half-dozen papers reporting the synthesis and characterization of seven-membered cyclic imino ethers were wrong (J. Am. Chem. Soc. 2018, DOI: 10.1021/jacs.8b10918). The compounds reported in the literature were actually N-acylated pyrrolidines, explaining their lack of reactivity. The sleuths developed a simple synthesis to prepare cyclic imino ethers and confirmed their structures with crystal X-ray diffraction. Ian D. Jenkins of Griffith University, who reported the synthesis of a misassigned seven-membered compound (Org. Biomol. Chem. 2008, DOI: 10.1039/b818310d), congratulates the team on correcting the literature. “We never considered that