Synthesis and characterization of two new chiral Kemp's acid derivatives: Structures fixed by a peculiar system of N-H...O, C-H...O and C-H...N hydrogen bonds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22810%2F16%3A43901729" target="_blank" >RIV/60461373:22810/16:43901729 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/16:43901729
Result on the web
<a href="http://dx.doi.org/10.1515/zkri-2016-1962" target="_blank" >http://dx.doi.org/10.1515/zkri-2016-1962</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1515/zkri-2016-1962" target="_blank" >10.1515/zkri-2016-1962</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and characterization of two new chiral Kemp's acid derivatives: Structures fixed by a peculiar system of N-H...O, C-H...O and C-H...N hydrogen bonds
Original language description
New chiral imide-oxazoline derivatives of Kemp's acid were synthesized with the aim to produce new ligands suitable for catalytic asymmetric reactions. Compound 1 is C18H28N2O3, systematic name (1R, 5S, 7R)-7-[(S)-4-tert-butyl-4,5-dihydrooxazole-2-yl]-1,5,7-trimethyl-3-azabicyclo-[3.3.1]-nonane-2,4-dione. Compound 2 is C21H26N2O3, systematic name (1R,5S,7R)-7-[(S)-4-benzyl-4,5-dihydrooxazole-2-yl]-1,5,7-trimethyl-3-azabicyclo-[3.3.1]-nonane-2,4-dione. Both compounds contain two molecules with very similar conformations in the asymmetric unit. The two structures were characterized by single crystal X-ray diffraction. DFT calculations of two possible distinct conformations were performed to elucidate the differences between the preferred conformation in vacuo and the one observed in the single crystal. Also, charges on the key atoms of the compounds were compared with a common ligand used for asymmetric transfer hydrogenation. ? 2016 Walter de Gruyter GmbH, Berlin/Boston 2016.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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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
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Zeitschrift fur Kristallographie - Crystalline Materials
ISSN
2194-4946
e-ISSN
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Volume of the periodical
231
Issue of the periodical within the volume
9
Country of publishing house
DE - GERMANY
Number of pages
9
Pages from-to
531-539
UT code for WoS article
000386050800004
EID of the result in the Scopus database
2-s2.0-84988530081