We gratefully acknowledge the Swedish Research Council Formas for generous financial support.

1. Gram-scala Sintesi di metile 6-oxo-3,4,6-triphenylhexanoate <ol><li> Lavaggio 1-etil-3-metil acetato imidazolio (EMIMAc) in un pallone a fondo rotondo su un evaporatore rotante a 10 mBar, 40 ° C per 1 ora. </li><li> Aggiungere 2,1 g di secco EMIMAc e 1,0 g di 1,3-difenil-2-propen-1-one per un Pallone da 100 ml a fondo tondo dotato di un agitatore magnetico. </li><li> Aggiungere 2.019 ml di metanolo e 2,3 g di cinnamaldeide al pallone. </li><li> A temperatura ambiente (22 ° C) sciogliere la miscela in 60 ml di diclorometano agitando per 1 min. </li><li> Successivamente aggiungere 0,37 ml di 1,8 diazabiciclo [5.4.0] undec-7-ene (DBU) alla miscela di agitazione (passo 1.4) e tappare il pallone a fondo tondo. </li><li> Mescolare con una ancoretta magnetica ad una velocità di 500 rpm a temperatura ambiente (22 ° C). </li><li> Controllare il completamento della reazione con 1 H NMR. 24 Cercare scomparsa del doppio legame del chalcone nell&#39;area 7,8 ppm. </li><li> Quando la reazione è raggiunto<html> completamento rimuovere le sostanze volatili in un evaporatore rotante a 10 mBar, 20 ° C per 15 min. </li><li> Aggiungere 50 ml di metanolo al residuo di sciogliere il EMIMAc mescolando con un bastoncino magnetico. </li><li> Rimuovere i solidi dalle pareti del pallone agitando violentemente con ancoretta magnetica ad una velocità di 750 rpm per 30 min. Se necessario, utilizzare una spatola per rimuovere residui solidi dalle pareti. </li><li> Filtrare la miscela su una fritta (dimensione dei pori 3). </li><li> Lavare con altri 20 ml di metanolo. Se si desidera il riciclaggio del EMIMAc evaporare il filtrato metanolica. (passo 2.1). </li><li> Sempre sul fritta, dividere delicatamente il panello di filtrazione (dal punto 1.11) in pezzi più piccoli con una spatola e trasferire i solidi tramite una tramoggia ad un pallone a fondo rotondo pre-pesato e asciugare i solidi sotto vuoto. </li><li> Pesare il pallone e calcolare il rendimento. </li><li> Analizzare il prodotto da 1 H NMR (punto 1.7). Confronta con spettri riportati. 24 </li></ol>title &quot;&gt; 2. Riciclaggio di EMIMAc <ol><li> Rimuovere le sostanze volatili dalla miscela metanolica (dal punto 1.12) sotto pressione ridotta di 10 mbar, a 40 ° C per 30 min. </li><li> Analizzare l&#39;olio risultante da 1H NMR e 13 C NMR per controllare che EMIMAc è presente. 24 </li><li> Utilizzare il EMIMAc riciclato a partire dal punto 1.2. </li></ol> 3. gelificazione <ol><li> Preparazione di una soluzione madre <ol><li> Aggiungere 200 mg di metil 6-oxo-3,4,6-triphenylhexanoate (il prodotto dal punto 1.15) e di una ancoretta magnetica di una fiala. Aggiungere 2,0 ml di diclorometano per sciogliere il chetoestere. Mescolare fino a quando tutto si è dissolto. </li></ol></li><li> Gelificazione <ol><li> Aggiungere 50 ml di eptano in un becher da 500 ml. Aggiungere 1,5 ml della soluzione madre al eptano. Mescolate rapidamente per garantire un&#39;adeguata miscelazione e lasciare riposare senza agitazione a temperatura ambiente finché non si verifica gelificazione. </li></ol></li></ol>

<ol>
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The authors have nothing to disclose.

Sulla base anti configurazione beta determinata mediante analisi ai raggi X di chetoestere 3 e l&#39;indagine meccanicistica proposto da Bode e collaboratori 30 il seguente percorso reazione viene suggerito (Figura 5). Deprotonazione dell&#39;IL genera specie NHC; NHC reagisce con l&#39;aldeide insaturo per formare il Breslow intermedio I. Il Breslow intermedio e il chalcone reagire in reazione di benzoino per formare diene II. Intermedio II subisce un riarrangiamento ossi-Cope via d...

<img alt="TOC 1" src="/files/ftp_upload/53213/53213TOC.jpg" /> (Sopra) sintesi tricomponente di 1,6-chetoesteri: una nuova classe di gelators basso peso molecolare. I liquidi ionici (ILS) hanno elevata stabilità, bassa volatilità, non infiammabilità e hanno quindi reso attenzione come mezzo di reazione sicure e solventi ideali per il riciclaggio. 1-3 imidazoliums dialchil sono un certo tipo di liquidi ionici che, in presenza di una base , può essere deprotonato rendere un carbene N-eterociclico (NHC). 4 Nel campo dell&#39;organocatalisi, NHCs, operando sotto percorsi di reazione distinti, hanno trovato uso diffuso in un&#39;ampia gamma di reazioni generiche. 5-11 Nonostante questo, la connessione tra ILs e legame CC Forming NHC-catalisi è relativamente inesplorato. Tuttavia, NHCs derivato da ILs sono stati segnalati per catalizzare reazioni di formazione di legami CC, come la condensazione benzoino e la reazione Stetter. 12-22 Ad esempio, Davis et al. Hanno dimostrato che ILs derivati ​​da thiazoliums N-alchil servono come precatalysts nel formazione di benzoino dal benzaldeide. 12 Più di recente, Chen e colleghi di lavoro ampliato questo concetto con un imidazolio basato IL, 1-etil-3-metil imidazolio acetato (EMIMAc), per eseguire la condensa benzoino, il 5-idrossimetilfurfurale (HMF) per generare 5,5 &#39;-di (idrossimetil) Furoin (DHMF). 23 Dato che ILs sono disponibili in commercio e offrono un modo economico di generare NHCs, siamo stati interessati a indagare quello che altri tipi di reazioni ILs potrebbe svolgere. A tal fine, abbiamo scoperto che dialchilici imidazoliums potrebbero efficacemente essere utilizzati come precatalysts nel coniugato additi formalesu aldeidi insature a calconi (figura 1) dà 1,6-chetoesteri. Il più efficiente IL, EMIMAc, promuove una forte reazione stereoselettiva tra cinnamaldeide e calcone. La reazione avviene con alta preferenza per l&#39;anti -diastereomer e gli 1,6-chetoesteri può essere isolato con rese fino al 92%. 24,25,26 <img alt="Figura 1" src="/files/ftp_upload/53213/53213fig1.jpg" /> Figura 1: IL-mediata tricomponente, addizione stereoselettiva di cinnamaldeide a calconi.

<table>
	<tbody>
		<tr>
			<td>1-ethyl-3-methyl imidazolium acetate</td>
			<td>Aldrich</td>
			<td>51053-100G-F</td>
			<td>Produced by BASF &#8805;90%, dried on a rotary evaporated before use (10 mBar, 40 &#176;C, 1h) 
			CAS NUMBER: 143314-17-4</td>
		</tr>
		<tr>
			<td>1,3-diphenyl-2-propen-1-one</td>
			<td>Aldrich</td>
			<td>11970-100G</td>
			<td>98.0% 
			CAS NUMBER: 94-41-7</td>
		</tr>
		<tr>
			<td>trans-cinnamaldehyde&#160;</td>
			<td>Aldrich</td>
			<td>C80687-25G</td>
			<td>99%, stored under nitrogen prior to use 
			CAS NUMBER: 14371-10-9</td>
		</tr>
		<tr>
			<td>1,8-Diazobicyclo[5.4.0]undec-7-ene</td>
			<td>Aldrich</td>
			<td>139009-25G</td>
			<td>98% 
			CAS NUMBER: 6674-22-2</td>
		</tr>
		<tr>
			<td>Methanol</td>
			<td>Sigma-Aldrich</td>
			<td>32213N-2.5L</td>
			<td>puriss. P.a., ACS reagent, reag. ISO, reag. Ph. Eur. &#8805;99.8% (GC) 
			CAS NUMBER: 67-56-1</td>
		</tr>
		<tr>
			<td>Dichloromethane</td>
			<td>Fischer Chemical</td>
			<td>D/1852/17X</td>
			<td>Analytic reagent grade, stabilized with amylene 
			CAS NUMBER:9/2/1975</td>
		</tr>
		<tr>
			<td>n-Heptane</td>
			<td>Fischer Chemical</td>
			<td>H/0160/17X</td>
			<td>Analytic reagent grade 
			CAS NUMBER: 142-82-5</td>
		</tr>
	</tbody>
</table>

highly stereoselective synthesis of 1,6-ketoesters mediated by ionic liquids: a three-component reaction enabling rapid access to a new class of low molecular weight gelators

In organic chemistry ionic liquids (ILs) have emerged as safe and recyclable reaction solvents. In the presence of a base ILs can be deprotonated to form catalytically active N-Heterocyclic Carbenes (NHCs). Here we have used ILs as precatalysts in the addition of &#945;,&#946;-unsaturated aldehydes to chalcones to form 1,6-ketoesters, incorporating an anti-diphenyl moiety in a highly stereoselective fashion. The reaction has a broad substrate scope and several functional groups and heteroaromatics can be integrated into the ketoester backbone in generally good yields with maintained stereoselectivity. The reaction protocol is robust and scalable. The starting materials are inexpensive and the products can be obtained after simple filtration, avoiding solvent-demanding chromatography. Furthermore, the IL can be recycled up to 5 times without any loss of reactivity. Moreover, the 1,6-ketoester end product is a potent gelator in several hydrocarbon based solvents. The method enables rapid access to and evaluation of a new class of low molecular weight gelators (LMWGs) from recyclable and inexpensive starting materials.

Come esemplificato sopra, EMIMAc servire come precatalyst nel coniugato aggiunta formale α, β-insaturo aldeidi a calconi. Altri commercialmente disponibili imidazolio ILs base come il cloruro di 1-etil-3-methylimidazolium (EMIMCl) e cloruro di 1-butil-3-methylimidazolium (BMIMCl) sono stati esaminati, tuttavia, queste reazioni sono svolte in rese inferiori che indicano che l&#39;anione acetato può essere importante per la reattività (Tabella 1, ingresso 1-3). 27,28 * ...

Watch this Scientific Journal Video about Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Ionic liquids (ILs) mediate fast, simple and cheap access to 1,6-ketoesters in high diastereoselectivities and good yields. The reaction protocol is robust and the 1,6-ketoesters can be obtained in gram scale after a simple filtration protocol. Moreover, the 1,6-ketoesters are potent gelators in hydrocarbon solvents.

Sintesi altamente stereoselettiva di 1,6-chetoesteri Mediata da liquidi ionici: una reazione a tre componenti Abilitazione accesso rapido a una nuova classe di basso peso molecolare Gelators

In organic chemistry ionic liquids (ILs) have emerged as safe and recyclable reaction solvents. In the presence of a base ILs can be deprotonated to form ...

highly-stereoselective-synthesis-16-ketoesters-mediated-ionic-liquids

Research

JoVE Journal

Chemistry

8.6K Views.  Chalmers University of Technology. Ionic liquids (ILs) mediate fast, simple and cheap access to 1,6-ketoesters in high diastereoselectivities and good yields. The reaction protocol is robust and the 1,6-ketoesters can be obtained in gram scale after a simple filtration protocol. Moreover, the 1,6-ketoesters are potent gelators in hydrocarbon solvents. 

Video: Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators