Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates

Yuko Kawanami, Tamara C.S. Pace, Jun Ichi Mizoguchi, Toshiharu Yanagi, Masaki Nishijima, Tadashi Mori, Takehiko Wada, Cornelia Bohne, Yoshihisa Inoue

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41 Citations (Scopus)

Abstract

(Figure Presented) The photochirogenesis of 2-anthracenecarboxylic acid (AC) complexed to a hydrogen-bonding template (TKS159) was investigated to obtainmechanistic information on how chirogenesis is achieved for the dimerization of AC. Complexation of AC to TKS159 leads to the shielding of one of the two surfaces of the prochiral AC molecule. The two diastereomeric AC-TKS complexes, i.e., re-AC-TKS and si-AC-TKS, were characterized by changes in the UV-vis, fluorescence, and circular dichroism spectra and excited-state lifetimes. The ee is not simply determined by the diastereomeric ratio of the re- and si-AC-TKS complexes but also depends on the relative lifetimes of the diastereomeric complexes. The relative population of the re and si complexes was calculated from the enantiomeric excess (ee) for the products, taking into account the relative lifetimes of the two complexes. These studies established a protocol that can be used to reveal the mechanism for photochirogenesis by investigating the ground state and the excited state behavior of supramolecular systems.

Original languageEnglish
Pages (from-to)7908-7921
Number of pages14
JournalJournal of Organic Chemistry
Volume74
Issue number20
DOIs
Publication statusPublished - 2009 Oct 16

ASJC Scopus subject areas

  • Organic Chemistry

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