A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins

Cheng Yang, Masaki Nishijima, Asao Nakamura, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The enantiodifferentiating [4+4] photocyclodimerization of anthracenecarboxylic acid (AC) mediated by native, mono- and di-3,6-anhydro-γ-cyclodextrins was investigated in both aqueous solution and solid-state. The solid-state photolyses gave inherently disfavored head-to-head photodimers in much higher chemical and optical yields than in the aqueous solution.

Original languageEnglish
Pages (from-to)4357-4360
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number25
DOIs
Publication statusPublished - 2007 Jun 18
Externally publishedYes

Fingerprint

Stereoselectivity
Cyclodextrins
Photolysis
Acids
anthracene-1-carboxylic acid

Keywords

  • 3,6-Anhydro-γ-cyclodextrin
  • Anthracenecarboxylic acid
  • Photocyclodimerization
  • Solid-state

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins. / Yang, Cheng; Nishijima, Masaki; Nakamura, Asao; Mori, Tadashi; Wada, Takehiko; Inoue, Yoshihisa.

In: Tetrahedron Letters, Vol. 48, No. 25, 18.06.2007, p. 4357-4360.

Research output: Contribution to journalArticle

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