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

作者：Bregier Frederique; Karuppannan Sekar; Chambron Jean Claude^*

来源：European Journal of Organic Chemistry, 2012, 2012(10): 1920-1925.

DOI：10.1002/ejoc.201101604

• Cyclodextrins
• Cyclophanes
• Cyclotrimerization
• Template synthesis
• Diastereoselectivity

A hybrid C3-symmetric cavitand 1, in which permethylated alpha-cyclodextrin (PM alpha-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 approximate to 6:1), the chirality of the alpha-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.

• 出版日期2012-4