6533b858fe1ef96bd12b56d1

RESEARCH PRODUCT

A Hybrid Cavitand Made by Capping Permethylated α-Cyclodextrin with Cyclotriveratrylene

Sekar KaruppannanFrédérique BrégierJean-claude Chambron

subject

chemistry.chemical_classificationIntramolecular reactionCyclodextrinChemistryStereochemistryOrganic ChemistryCavitandCyclotriveratryleneInclusion compoundchemistry.chemical_compoundVanillyl alcoholPhysical and Theoretical ChemistryChirality (chemistry)Cyclophane

description

A hybrid C 3 -symmetric cavitand 1, in which permethylated α-cyclodextrin (PM α-CDX) is capped with cyclotriveratrylene (CTV), has been prepared in 8 % yield by intramolecular cyclization of a vanillyl alcohol derivative attached to the primary rim of the CDX platform. The reaction proceeds diastereoselectively (dr ≈ 6:1), the chirality of the α-glucopyranosyl units controlling the chirality of the CTV component. Interestingly, in polar solvents, 1 shows self-complexation properties as the primary methoxy groups of the CDX component are directed towards the CTV cavity.

yearjournalcountryeditionlanguage
2012-02-21European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201101604