Abstract
The biphasic palladium catalyzed cleavage of water-insoluble N-substituted- O-allylic urethanes in the presence of randomly methylated β-cyclodextrins has been investigated with the aim of performing substrate-selective catalytic reactions. By using different pairs of structural isomers, it was found that the substrate selectivity depends strongly on the water solubility and the structure of isomers. So, a high substrate selectivity can only be observed with highly water-insoluble isomers that present pronounced structural differences. Furthermore, the size-fit concept which postulates the highest reactivity for the best size-matched host–guest pair provides a very useful tool for predicting the values of substrate selectivity.
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