Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F06%3A00003284" target="_blank" >RIV/00216275:25310/06:00003284 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Novel nitrogen ligands based on imidazole derivatives and their application in asymmetric catalysis

Original language description

Recently prepared chiral amines have been used in the preparation of novel tridentate ligands based on an imidazole ring with an additional (hetero)ring. The synthesis was carried out by the reaction of chiral amines with suitable aldehydes (2-phenylimidazole-4-carbaldehyde, 2-hydroxybenzaldehyde or pyridine-2-carbaldehyde) under reductive conditions (H2/Pd or NaBH4). All ligands prepared showed strong hydrogen bonds in d6-DMSO solution, which resulted in hindered imidazole tautomerism. The observed hindered tautomerism was studied by 1H NMR spectroscopy. The structures of the prepared ligands were also confirmed by APCI mass spectroscopy. Both chiral amines and tridentate compounds have been applied as ligands in copper (II)-catalyzed nitroaldol reactions (Henry reaction). Various reaction conditions for the Henry reaction have been studied (influence of temperature, molar ratio, solvent or copper (II) precursors). The compounds prepared with the two imidazole rings showed fast reacti

Czech name

Nové dusíkaté ligandy obsahující imidazolový kruh a jejich použití v asymetrické katalýze

Czech description

Dříve připravené chirální aminy byly použity pro přípravu cových tridentálních ligandů založených na imidazolovém systému doplněném o další (hetero)cyklus. Chirální aminy a tridentáoní ligandy byly použity jako ligandy dojmocnou mědí katalyzované nitroaldolové reakce (Henryho reakce). Systémy obsahující dva imidazolové kruhy vykazují krátké reakčí časy ve srovnání s ostatními aminy.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/LA%20131" target="_blank" >LA 131: IUPAC General Assembly - National Representative Commission III.2</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

Confidentiality

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

Name of the periodical

Tetrahedron: Asymmetry

ISSN

0957-4166

e-ISSN

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Volume of the periodical

17

Issue of the periodical within the volume

6

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

8

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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