Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F08%3A00007557" target="_blank" >RIV/00216275:25310/08:00007557 - 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

Utilizing terpene derivatives in the synthesis of annulated terpene-imidazoles with application in the nitroaldol reaction

Original language description

Two classes of terpene derivatives (diketones and monoximes) were condensed into annulated terpeneimidazoles using two general methods. Method A, involving the condensation of terpene diketones and aldehydes, gave lower yields than Method B, which employed terpene monoximes and amines. The mechanism of Method B is discussed. Using both methods, overall 11 new imidazole ligands were synthesized and fully characterized. The molecular structures of the side product 16 and intermediate 4b were also characterized by X-ray analysis. Regarding 1a, N-methylation and subsequent ortho-lithiation and quenching with diphenylphosphinechloride were proven. The synthesized ligands were tested in the Henry reaction providing reaction times 24?72 h and enantioselectivities up to 32% especially for the pyridine 2-substituted ligands 1c, 2c, 3b and N,P-ligand 17.

Czech name

Využití terpenových derivátů v syntéze terpen-imidazolů s aplikací v nitroaldolové reakci

Czech description

Dvě třídy derivátů terpenů (diketony a monoximy) byly kondenzovány na deriváty imidazolu s využitím dvou metod. Metoda A zahrnuje kondenzaci diketonů s aldehydy, metoda B pak reakci monoximů s aminy. Mechanismus metody je rovněž diskutován. Celkem bylo syntetizováno a charakterizováno 11 nových derivátů imidazolu. Dva intermediáty/vedlejší produkty byly rovněž charakterizovány pomoci X-ray analýzy. Syntetizované ligandy byly aplikovány v asymetrické Henryho reakci, kdy bylo dosaženo reakčních časů 24-72h a enantioselektivit do 32%.

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/GP203%2F07%2FP013" target="_blank" >GP203/07/P013: Nonracemic nitrogen ligands based on imidazole - potencial catalysts of asymmetric reactions.</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2008

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

19

Issue of the periodical within the volume

21

Country of publishing house

GB - UNITED KINGDOM

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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