Spherical Amides with Symmetry: Improved Synthetic Approach and Structural/Optical Analysis.

Molecules

Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi 274-8510, Chiba, Japan.

Published: February 2025


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Article Abstract

A spherical amide with symmetry was synthesized by a one-step cyclization reaction using triphenylphosphine and hexachloroethane as coupling reagents. This method enabled synthesis of -benzyl and -allyl derivatives, which could not be obtained by the previously reported method. The optical resolution of each compound was measured, and their electronic circular dichroism spectra revealed that they were mirror images. The high structural symmetry resulted in a higher Δε (molar absorption difference against right or left circular polarization: - value compared to that of another structural isomer synthesized previously. The absolute structure of the enantiopure crystal of the -benzyl derivative was determined using the Flack parameter obtained by X-ray crystallographic analysis.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11901929PMC
http://dx.doi.org/10.3390/molecules30051074DOI Listing

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