Chiral recyclable Cu(II)-catalysts in nitroaldol reaction of aldehydes with various nitroalkanes and its application in the synthesis of a valuable drug (R)-isoproterenol

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F13%3A00394207" target="_blank" >RIV/61388963:_____/13:00394207 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.apcata.2013.03.032" target="_blank" >http://dx.doi.org/10.1016/j.apcata.2013.03.032</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.apcata.2013.03.032" target="_blank" >10.1016/j.apcata.2013.03.032</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chiral recyclable Cu(II)-catalysts in nitroaldol reaction of aldehydes with various nitroalkanes and its application in the synthesis of a valuable drug (R)-isoproterenol

Popis výsledku v původním jazyce

Chiral dimeric macrocyclic salen ligands 1'a-c and [H-4]salen 2'a-c derived from (1R,2R)-(-)-1,2-diaminocyclohexane, (1R,2R)-(+)-1,2-diphenyl-1,2-diaminoethane, and (R)-(+)-1,1'-binaphthyl-2,2'-diamine with 5,5'-(piperazine-1,4-diylbis(methylene)-bis-(3-tert-butyl-2-hydroxybenzaldehyde) were prepared. Cu(II) complexes 1a-c and 2a-c were generated in situ by the interaction of different source of copper(II) salts with chiral dimeric macrocyclic salen ligands 1'a-c and 2'a-c and used for asymmetric nitroaldol reaction of various aromatic and aliphatic aldehydes with various nitroalkanes at RT (27 +/- 2 degrees C). Excellent yields (98% with respect to the aldehyde) of beta-nitroalcohols with high enantioselectivity (ee, similar to 99%) was achieved in case of 2-fluorobenzaldehyde and nitromethane in ca. 20 h with the use of chiral dinuclear macrocyclic [H4]salen Cu(II)-2'a complex. This protocol also worked well with nitroethane and 2-nitropropane with several aldehydes to furnish the co

Název v anglickém jazyce

Chiral recyclable Cu(II)-catalysts in nitroaldol reaction of aldehydes with various nitroalkanes and its application in the synthesis of a valuable drug (R)-isoproterenol

Popis výsledku anglicky

Chiral dimeric macrocyclic salen ligands 1'a-c and [H-4]salen 2'a-c derived from (1R,2R)-(-)-1,2-diaminocyclohexane, (1R,2R)-(+)-1,2-diphenyl-1,2-diaminoethane, and (R)-(+)-1,1'-binaphthyl-2,2'-diamine with 5,5'-(piperazine-1,4-diylbis(methylene)-bis-(3-tert-butyl-2-hydroxybenzaldehyde) were prepared. Cu(II) complexes 1a-c and 2a-c were generated in situ by the interaction of different source of copper(II) salts with chiral dimeric macrocyclic salen ligands 1'a-c and 2'a-c and used for asymmetric nitroaldol reaction of various aromatic and aliphatic aldehydes with various nitroalkanes at RT (27 +/- 2 degrees C). Excellent yields (98% with respect to the aldehyde) of beta-nitroalcohols with high enantioselectivity (ee, similar to 99%) was achieved in case of 2-fluorobenzaldehyde and nitromethane in ca. 20 h with the use of chiral dinuclear macrocyclic [H4]salen Cu(II)-2'a complex. This protocol also worked well with nitroethane and 2-nitropropane with several aldehydes to furnish the co

Druh

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

CEP obor

CF - Fyzikální chemie a teoretická 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

2013

Kód důvěrnosti údajů

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

Název periodika

Applied Catalysis A - General

ISSN

0926-860X

e-ISSN

—

Svazek periodika

459

Číslo periodika v rámci svazku

May

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

97-105

Kód UT WoS článku

000320477700013

EID výsledku v databázi Scopus

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