Supramolecular enantiodifferentiating photoisomerization of cyclooctene with modified β-cyclodextrins: critical control by a host structure
- 29 October 2007
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 3,p. 374-376
- https://doi.org/10.1039/b714300a
Abstract
Enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by m-methoxybenzoyl-β-cyclodextrin gave chiral (E)-isomers in up to 46% enantiomeric excess, which is the highest value ever reported for supramolecular photochirogenesis with analogous hosts, thus demonstrating the crucial role of the sensitizer-spacer moiety in supramolecular photochirogenic systems.Keywords
This publication has 28 references indexed in Scilit:
- Entropy-Controlled Supramolecular Photochirogenesis: Enantiodifferentiating Z−E Photoisomerization of Cyclooctene Included and Sensitized by Permethylated 6-O-Modified β-CyclodextrinsThe Journal of Organic Chemistry, 2006
- Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z–E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-β-cyclodextrinChemical Communications, 2005
- Enantiodifferentiating [4+4] photocyclodimerization of 2-anthracenecarboxylate catalyzed by 6A,6X-diamino-6A,6X-dideoxy-γ-cyclodextrins: Manipulation of product chirality by electrostatic interaction, temperature and solvent in supramolecular photochirogenesisJournal of Photochemistry and Photobiology A: Chemistry, 2005
- Chiral PhotochemistryPublished by Taylor & Francis ,2004
- Enantioselective [4+2]‐Cycloaddition Reaction of a Photochemically Generated o‐Quinodimethane: Mechanistic Details, Association Studies, and Pressure EffectsChemistry – A European Journal, 2004
- Highly Enantioselective Intra- and Intermolecular [2 + 2] Photocycloaddition Reactions of 2-Quinolones Mediated by a Chiral Lactam Host: Host−Guest Interactions, Product Configuration, and the Origin of the Stereoselectivity in SolutionJournal of the American Chemical Society, 2002
- Use of Chirally Modified Zeolites and Crystals in Photochemical Asymmetric SynthesisJournal of the American Chemical Society, 2002
- Asymmetric Induction With Cyclodextrins: Photocyclization of Tropolone Alkyl EthersTetrahedron, 2000
- Asymmetric photochemical reactions in solutionChemical Reviews, 1992
- Asymmetric induction in benzoin by photolysis of benzaldehyde adsorbed in cyclodextrin cavitiesTetrahedron Letters, 1989