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Inherently Chiral Molecular Clips: Synthesis, Chiroptical Properties, and Application to Chiral Discrimination
Author(s) -
Fukuhara Gaku,
Madenci Süreyya,
Polkowska Jolanta,
Bastkowski Frank,
Klärner FrankGerrit,
Origane Yumi,
Kaneda Masayuki,
Mori Tadashi,
Wada Takehiko,
Inoue Yoshihisa
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601585
Subject(s) - enantiomer , optically active , specific rotation , adduct , chemistry , chirality (physics) , chiral column chromatography , stereochemistry , chiral derivatizing agent , optical rotation , absolute configuration , resolution (logic) , chiral symmetry , organic chemistry , physics , quantum mechanics , artificial intelligence , computer science , nambu–jona lasinio model , quark
Inherently chiral molecular clips (MCs), pseudoenantiomeric anti ‐ 1 and anti ‐ 2 , as well as mesoid syn ‐ 3 , were synthesized by diastereodifferentiating repetitive Diels–Alder reactions of the achiral bisdienophile 6 with chiral diene 5 generated in situ from (−)‐menthyl 3,4‐bis(dibromomethyl)benzoate 4 . These MCs were successfully separated by chiral HPLC to give optically active anti ‐ 1 and anti ‐ 2 and almost optically inactive syn ‐ 3 . The structures of anti ‐ 1 , anti ‐ 2 , and syn ‐ 3 were assigned by high‐resolution NMR and the absolute configurations of anti ‐ 1 and anti ‐ 2 were determined by the exciton‐chirality method. Optically active anti ‐ 2 can serve as a chiral host. It binds the HCl adduct of D ‐tryptophan methyl ester ( D ‐TrpOMe ⋅ HCl) 3.5 times stronger than the L ‐enantiomer ( K D / K L =3.5).
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