Macrocycle synthesis by chloride-templated amide bond formation
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Other documents of the author: Martí-Centelles, Vicente; Burguete, M. Isabel; Luis, Santiago V.
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Title
Macrocycle synthesis by chloride-templated amide bond formationDate
2016Publisher
American Chemical SocietyISSN
0022-3263; 1520-6904Type
info:eu-repo/semantics/articlePublisher version
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02676Subject
Abstract
A new family of pseudopeptidic macrocyclic
compounds has been prepared involving an anion-templated
amide bond formation reaction at the macrocyclization step.
Chloride anion was found to be the most efficient ... [+]
A new family of pseudopeptidic macrocyclic
compounds has been prepared involving an anion-templated
amide bond formation reaction at the macrocyclization step.
Chloride anion was found to be the most efficient template in
the macrocyclization process, producing improved macrocyclization
yields with regard to the nontemplated reaction.
The data suggest a kinetic effect of the chloride template,
providing an appropriate folded conformation of the openchain
precursor and reducing the energy barrier for the
formation of the macrocyclic product. [-]
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J. Org. Chem. 2016, 81, 2143−2147Rights
ACS AuthorChoice - This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
© 2016 American Chemical Society
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