Application of Glaser−Hay Diyne Coupling To Constrain Nα‑Amino Acid Amides via a N−N Bridge

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F19%3A73596986" target="_blank" >RIV/61989592:15310/19:73596986 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00179" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acscombsci.8b00179</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acscombsci.8b00179" target="_blank" >10.1021/acscombsci.8b00179</a>

Result language
angličtina
Original language name
Application of Glaser−Hay Diyne Coupling To Constrain Nα‑Amino Acid Amides via a N−N Bridge
Original language description
We present the application of a Glaser−Hay diyne coupling for the synthesis of conformationally constrained Nα-amino acid amides with different diyne ring sizes. Twelve-membered rings were the smallest rings that could be prepared by this approach. We observed the formation of triethylammonium adducts in the cases of smaller (10- and 11-membered) rings. Calculation of the conformational barriers for the cyclization reactions of various ring sizes demonstrated that the formation of amino acid-derived smaller rings by this reaction is thermodynamically unfavorable.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA16-06446S" target="_blank" >GA16-06446S: From Amino Acids to Nature-Inspired Molecular Scaffolds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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