Gelation of a π-Decorated Glutamate as a Homochiral Selective Self-assembly to Obtain Macroscopic Chiral Symmetry Breaking

KENTARO TASHIRO; TOSHIAKI TAKEI; ALEJANDRO M. FRACAROLI; HIROYOSHI OHTSU; MASAKI KAWANO; DAISUKE HASHIZUME

CHEMISTRY-AN ASIAN JOURNAL

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2022 vol. 17

1861-4728

An N-Fmoc and C-tBu-protected glutamate (1) bearing a phenanthrene moiety at the side residue crystalizes and gels to afford hetero- and homochiral assemblies, respectively, depending on its optical purity or solvent. When a non-stoichiometric mixture of enantiomers of 1 in acetonitrile was treated with the conditions that leave a mixture of gel and supernatant, it exhibited the selfdisproportionation of enantiomers with an enrichment of the major enantiomer in the gel. Under similar conditions, a racemic mixture of 1 also provided a gel/supernatant mixture, where the gel was enriched in either of L or D-form of 1 stochastically as the result of macroscopic chiral symmetry breaking in its gelation process.