Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate within γ-cyclodextrin cavity through chemical modification. Inverted product distribution and enhanced enantioselectivity

Asao Nakamura, Yoshihisa Inoue

Research output: Contribution to journalArticle

110 Citations (Scopus)

Abstract

In the enantiodifferentiating supramolecular photocyclodimerization of 2-anthracenecarboxylate using γ-cyclodextrin with a dicationic side chain, a dramatic switching of the product selectivity and a significant enhancement of the enantiomeric excess were achieved by introducing a flexible dicationic sidearm to native γ-cyclodextrin and also by lowering the temperature and solvent polarity.

Original languageEnglish
Pages (from-to)5338-5339
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number15
DOIs
Publication statusPublished - 2005 Apr 20

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Enantioselectivity
Cyclodextrins
Chemical modification
Electrostatics
Temperature
2-anthracenecarboxylate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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AB - In the enantiodifferentiating supramolecular photocyclodimerization of 2-anthracenecarboxylate using γ-cyclodextrin with a dicationic side chain, a dramatic switching of the product selectivity and a significant enhancement of the enantiomeric excess were achieved by introducing a flexible dicationic sidearm to native γ-cyclodextrin and also by lowering the temperature and solvent polarity.

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