Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• . Keywords: γ-cyclodextrin; naphthylallyl derivatives; regioselective alkylation; supramolecular properties; synthesis; Introduction Cyclodextrins [1] (CDs) are cyclic oligosaccharides with a cone-shaped cavity formed by α-1,4-linked D-glucopyranose units. The most widely used CDs are α-, β-, and γ-CD with

• polymers of CD–guest type [17]. Moreover, the double bond of the allyl group allows a subsequent conversion of these compounds to other regiospecifically monosubstituted γ-CD derivatives. Naphthylallyl derivatives of any CD have not been described yet. Supramolecular properties of the prepared derivatives

• for this reaction has to be prepared from γ-CD in two steps involving complicated chromatographic separations. Thus, the overall yields of the pure NA regioisomers were only 2–5%. Therefore, we turned our focus to developing another method for the preparation of naphthylallyl derivatives, which is