Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol

Yuko Kawanami, Shin Ya Katsumata, Jun Ichi Mizoguchi, Masaki Nishijima, Gaku Fukuhara, Cheng Yang, Tadashi Mori, Yoshihisa Inoue

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/p-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.

Original languageEnglish
Pages (from-to)4962-4965
Number of pages4
JournalOrganic letters
Volume14
Issue number18
DOIs
Publication statusPublished - 2012 Sep 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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