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A Hybrid Cavitand Made by Capping Permethylated α‐Cyclodextrin with Cyclotriveratrylene
Author(s) -
Brégier Frédérique,
Karuppannan Sekar,
Chambron JeanClaude
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101604
Subject(s) - cavitand , chemistry , chirality (physics) , cyclodextrin , derivative (finance) , yield (engineering) , stereochemistry , polar , crystallography , supramolecular chemistry , organic chemistry , crystal structure , materials science , astronomy , financial economics , economics , metallurgy , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.