4.4 Article

Toward reactant encapsulation for substrate-selectivity

期刊

TETRAHEDRON LETTERS
卷 53, 期 4, 页码 462-466

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.11.078

关键词

Cage compounds; Cryptands; Enzyme models; N Ligands; Schiff bases

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A synthetic tris-(bis-(aminomethyl)pyridine) receptor was prepared in excellent yields via reversible imine condensation strategy. Catalytic activity in Henry reactions of the corresponding copper(II) complex was studied. Capitalizing on previous works by Anslyn with related receptors, the dramatic increase in basicity induced by this type of complex on diketo-derivatives was used to perform a nucleophilic addition of a deprotonated substrate onto an electrophile within the cavity. Hence, a Lewis acid stabilized nitronate was reacted with various aldehydes. A notable preference for small reactants easily accommodated in the cavity over encumbered ones was observed, thus representing an example of substrate-selectivity. (C) 2011 Elsevier Ltd. All rights reserved.

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