Journal
TETRAHEDRON
Volume 61, Issue 20, Pages 4811-4817Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.03.017
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Selective decarboxylation of two alkylallylurethane isomers into alkylallylamines has been performed in a biphasic system by using randomly hydroxypropylated and methylated cyclodextrins as discriminating agents. Surprisingly, the presence of small organic hydrosoluble molecules such as amine or alcohol derivatives appeared to be crucial in the discriminating process. Indeed, it was clearly proved that the presence of such additives enhances greatly the substrate selectivity. For instance, the addition of triethylamine to the reaction medium allows to improve the discriminating power of methylated-p-cyclodextrin by a factor 7. These unexpected results were explained by considering the formation of ternary cyclodextrin/substrate/additive complexes. (c) 2005 Elsevier Ltd. All rights reserved.
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