New cup-shaped α-cyclodextrin derivatives and a study of their catalytic properties in oxidation reactions

A series of new α-cyclodextrin derivatives with a substituted propylene bridge attached to the 6-O's of the A,D-glucose units are reported. The compounds were prepared from the known 6A,6D-di-O-(prop-2-methylidene-1,3-dienyl)-hexadeca-O-benzyl-α-cyclodextrin, which was transformed into 6A,6D-di-O-(prop-2-methyl-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-formyl-2-hydroxy-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-aminomethyl-2-hydroxy-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-hydroxymethylidene-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-formyl-1,3-dienyl)-α-cyclodextrin, 6A,6D-di-O-(prop-2-carboxy-1,3-dienyl)-α-cyclodextrin and 6A,6D-di-O-(prop-2-methoxycarbonyl-1,3-dienyl)-α-cyclodextrin. The new compounds were evaluated for their ability to affect amine and alcohol oxidations in the presence of hydrogen peroxide.