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Issue 5, 2013
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Cyclopeptoids: a novel class of phase-transfer catalysts

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Abstract

The synthesis, complexation properties and catalytic activities under phase-transfer (PT) conditions of differently substituted cyclohexapeptoids are reported. Association constants, for small cationic alkali, and catalytic performances, in a model nucleophilic substitution, are comparable to those of representative crown ethers. Noteworthy, the N-[2-(2-methoxyethoxy)ethyl] side chain derivative presents a catalytic efficiency comparable to that of crypt-222, and higher than some commonly used quaternary ammonium salts and crown ethers. Moreover its association constant for Na+ complexation proved to be higher when compared with dicyclohexyl-18-crown-6. The synthesized cyclohexapeptoids represent the first example of these peptidomimetics in PT catalysis, anticipating interesting applications in biphasic PT methodology.

Graphical abstract: Cyclopeptoids: a novel class of phase-transfer catalysts

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Supplementary files

Article information


Submitted
07 Sep 2012
Accepted
16 Oct 2012
First published
17 Oct 2012

Org. Biomol. Chem., 2013,11, 726-731
Article type
Paper

Cyclopeptoids: a novel class of phase-transfer catalysts

G. D. Sala, B. Nardone, F. De Riccardis and I. Izzo, Org. Biomol. Chem., 2013, 11, 726
DOI: 10.1039/C2OB26764K

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