Organic Reactions Mediated by Cyclodextrins

Self-Assembled Nanoreactors

“…[6][7][8][9] From the early 1970s on, cyclodextrins (CDs), naturally abundant cavity molecules, have been extensively used as binding sites in supramolecular catalysts. [10][11][12][13] A myriad of functionalized cyclodextrins have shown to be selective catalysts for ester hydrolysis. 14 representative example is Breslow's mimic of the enzyme ribonuclease A, 14,18 which works according to principles of acid-base catalysis ( Figure 1a).…”

A kinetic study of the basic hydrolysis of 2-phenylethyl nitrite in the presence of borate buffer and β-cyclodextrin

“…This implies that the presence of β-CD favors this step, and that β-CD directly participates in the reaction. In other words, the complex β-CD-RONOB(OH) 3 is more reactive than the uncomplexed RONOB(OH) 3 . According to this, the kinetic constant associated with the first step, at a fixed pH value, increases with increasing β-CD concentration giving rise to a saturation value.…”

“…2 Chemical reactions pertaining to the included guest may take place, and the effects of inclusion on the reactivity vary widely depending on the nature of the guest, the CD, and the reaction examined. 3 The CD may take part directly in the reaction, interacting with substrate through one (or more) hydroxylic group (or their conjugate base, depending on the pH value) placed on the secondary rim. 4 It has been found that the rate of the reaction is either greatly reduced, which has led to the use of CDs as stabilizers, 5 or increased owing to their effect on enthalpic and/or entropic factors.…”

Cyclodextrins in Asymmetric and Stereospecific Synthesis

“…Cyclodextrins have long been used in organic synthesis as promoters or catalysts of different reactions [2]. They are very attractive as components of artificial enzymatic systems [3] and can also be used as stabilizers for the nanodimensional metallic catalysts, thus enhancing their catalytic activity [4].…”