Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F19%3A73596934" target="_blank" >RIV/61989592:15110/19:73596934 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/19:73596934
Result on the web
<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.joc.8b02465" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.joc.8b02465</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.8b02465" target="_blank" >10.1021/acs.joc.8b02465</a>
Alternative languages
Result language
angličtina
Original language name
Configuration-Dependent Medium-Sized Ring Formation: Chiral Molecular Framework with Three-Dimensional Architecture
Original language description
This report describes a configuration-dependent [6+8+5] fused ring formation via a tandem cyclic N-acyliminium-nucleophilic addition reaction. Cyclization of the acyclic precursor prepared on the solid phase using L-Ser and racemic mixture of Fmoc-trans-2-aminocyclohexane carboxylic acid predominantly yielded the cyclic diastereomer with the (1R,2R)-2-aminocyclohexane moiety rather than the tricyclic diastereomer from the (1S,2S)-enantiomer. In contrast, the model compound prepared with D-Ser predominantly cyclized with the (1S,2S)-2-aminocyclohexane carboxylic acid substrate. The outcome of the cyclization was not influenced by the type of resin, the spacer or the N-substituent. The analogous synthesis of the [6+7+5] fused ring system yielded an inseparable diastereomers in a 1:0.6 ratio.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
JOURNAL OF ORGANIC CHEMISTRY
ISSN
0022-3263
e-ISSN
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Volume of the periodical
84
Issue of the periodical within the volume
2
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
636-644
UT code for WoS article
000456632800016
EID of the result in the Scopus database
2-s2.0-85059645550