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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/60461373:22310/16:43901729

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Zeitschrift fur Kristallographie - Crystalline Materials

ISSN

2194-4946

e-ISSN

—

Svazek periodika

231

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

9

Strana od-do

531-539

Kód UT WoS článku

000386050800004

EID výsledku v databázi Scopus

2-s2.0-84988530081