Phenylalanine-Derived Imidazolines Bearing Heteroaromatic Pendants: Synthesis, Characterization, and Application in the Asymmetric Henry Reaction

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F15%3A39899751" target="_blank" >RIV/00216275:25310/15:39899751 - isvavai.cz</a>

Výsledek na webu

<a href="http://onlinelibrary.wiley.com/doi/10.1002/hlca.201500128/abstract" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/hlca.201500128/abstract</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/hlca.201500128" target="_blank" >10.1002/hlca.201500128</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Phenylalanine-Derived Imidazolines Bearing Heteroaromatic Pendants: Synthesis, Characterization, and Application in the Asymmetric Henry Reaction

Popis výsledku v původním jazyce

Starting from L-phenylalanine, (2S)-3-phenylpropane-1,2-diamine has been prepared and used as building block for the construction of the imidazoline ring. Four new optically pure NH-imidazolines bearing different six-membered heteroaromatic substituentson the C(2) position have been prepared and subsequently N-modified. N-Substitution afforded two regioisomers that were separated. Some of them proved to be instable and hydrolyzed to diamides. The molecular structures of NH-imidazolines, both N-substituted regioisomers, as well as diamides, were unambiguously confirmed by X-ray-analysis and NMR spectra. The successfully prepared imidazolines, as well as diamides, were applied as catalysts in a Cu(II)-catalyzed Henry reaction achieving 26-98% chemical yields and enantiomeric excesses of 3-42%.

Název v anglickém jazyce

Phenylalanine-Derived Imidazolines Bearing Heteroaromatic Pendants: Synthesis, Characterization, and Application in the Asymmetric Henry Reaction

Popis výsledku anglicky

Starting from L-phenylalanine, (2S)-3-phenylpropane-1,2-diamine has been prepared and used as building block for the construction of the imidazoline ring. Four new optically pure NH-imidazolines bearing different six-membered heteroaromatic substituentson the C(2) position have been prepared and subsequently N-modified. N-Substitution afforded two regioisomers that were separated. Some of them proved to be instable and hydrolyzed to diamides. The molecular structures of NH-imidazolines, both N-substituted regioisomers, as well as diamides, were unambiguously confirmed by X-ray-analysis and NMR spectra. The successfully prepared imidazolines, as well as diamides, were applied as catalysts in a Cu(II)-catalyzed Henry reaction achieving 26-98% chemical yields and enantiomeric excesses of 3-42%.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Helvetica Chimica Acta

ISSN

0018-019X

e-ISSN

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Svazek periodika

98

Číslo periodika v rámci svazku

10

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

13

Strana od-do

1351-1363

Kód UT WoS článku

000362958200002

EID výsledku v databázi Scopus

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