scholarly journals Cross-metathesis reaction of α- and β-vinyl C-glycosides with alkenes

2015 ◽  
Vol 11 ◽  
pp. 1392-1397 ◽  
Author(s):  
Ivan Šnajdr ◽  
Kamil Parkan ◽  
Filip Hessler ◽  
Martin Kotora
Keyword(s):  
Metathesis Reaction ◽  
Simple Method ◽  
Cross Metathesis ◽  
Terminal Alkenes ◽  
The Cross

Cross-metathesis of α- and β-vinyl C-deoxyribosides and α-vinyl C-galactoside with various terminal alkenes under different conditions was studied. The cross-metathesis of the former proceeded with good yields of the corresponding products in ClCH2CH2Cl the latter required the presence of CuI in CH2Cl2 to achieve good yields of the products. A simple method for the preparation of α- and β-vinyl C-deoxyribosides was also developed. In addition, feasibility of deprotection and further transformations were briefly explored.

scholarly journals Relay cross metathesis reactions of vinylphosphonates

2014 ◽  
Vol 10 ◽  
pp. 1933-1941 ◽  
Author(s):  
Raj K Malla ◽  
Jeremy N Ridenour ◽  
Christopher D Spilling
Keyword(s):  
Reaction Mechanism ◽  
Metathesis Reaction ◽  
Grubbs Catalyst ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
Terminal Alkenes ◽  
The Cross

Dimethyl (β-substituted) vinylphosphonates do not readily undergo cross metathesis reactions with Grubbs catalyst and terminal alkenes. However, the corresponding mono- or diallyl vinylphosphonate esters undergo facile cross metathesis reactions. The improved reactivity is attributed to a relay step in the cross metathesis reaction mechanism.

Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

2015 ◽  
Vol 68 (12) ◽  
pp. 1815 ◽  
Author(s):  
Steven-Alan G. Abel ◽  
Wesley J. Olivier ◽  
Richard L. Pederson ◽  
Alex C. Bissember ◽  
Jason A. Smith
Keyword(s):  
The Self ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
The Cross

(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

Regulation of the degree of blockiness of the norbornene–cyclooctene copolymer synthesized via the cross-metathesis reaction

2016 ◽  
Vol 58 (3) ◽  
pp. 292-297 ◽  
Author(s):  
Yu. I. Denisova ◽  
M. L. Gringolts ◽  
L. B. Krentsel’ ◽  
G. A. Shandryuk ◽  
A. D. Litmanovich ◽  
...  
Keyword(s):  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross

Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-d-ribopyranose ring system donors

RSC Advances ◽  
2014 ◽  
Vol 4 (38) ◽  
pp. 19794-19799 ◽  
Author(s):  
Omar Boutureira ◽  
M. Isabel Matheu ◽  
Yolanda Díaz ◽  
Sergio Castillón
Keyword(s):  
Microwave Irradiation ◽  
Ring System ◽  
Metathesis Reaction ◽  
Vinyl Sulfide ◽  
Cross Metathesis ◽  
The Cross ◽  
Flexible Metal ◽  
Phenyl Vinyl

Microwave irradiation effectively accelerates the cross-metathesis reaction of 2-deoxy-d-ribose hydroxyalkene and derivatives with electron-rich phenyl vinyl sulfide using commercially available ruthenium-based catalysts, thus providing a flexible metal-mediated route to 2,3-dideoxy-d-ribopyranose ring system donors.

scholarly journals In-Depth Lipidome Annotation Through an Operatively Simple Method Combining Cross-Metathesis Reaction and Tandem Mass Spectrometry

2021 ◽  
Author(s):  
Romain MAGNY ◽  
Anne Regazzetti ◽  
Karima Kessal ◽  
Christophe Baudouin ◽  
Stéphane Mélik-Parsadaniantz ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Tandem Mass ◽  
Metathesis Reaction ◽  
Simple Method ◽  
Cross Metathesis ◽  
Corneal Toxicity ◽  
Vitro Model ◽  
Structure Annotation

The in-depth knowledge of lipid biological functions calls for a comprehensive lipid structure annotation that implies implementing a method to locate fatty acids unsaturations. To address this challenge we have associated Grubbs' cross metathesis reaction and liquid chromatography hyphenated to tandem mass spectrometry. The pretreatment of lipids containing samples by Grubbs' catalyst and an appropriate alken generates substituted lipids through cross-metathesis reaction under mild, chemoselective and highly reproducible conditions. A systematic LC-MS/MS analysis of the reaction mixture allows locating unambigouslt the double bounds in fatty acid side chains. This method has en successfully applied at a nanomole scale to commerical standard mixtures as well as in lipid extracts from an in vitro model of corneal toxicity.<br><div><a></a><a></a><a></a><a></a></div><div><a></a><a></a><a></a> </div>

Study of the Cross-Metathesis Reaction of α-Hydroxy β,γ-Unsaturated Amides towards a Rapid and Flexible Total ­Synthesis of Symbioramide and its Isomer

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 230-234 ◽  
Author(s):  
Alexandre Gratais ◽  
Samir Bouzbouz
Keyword(s):  
Methyl Ester ◽  
Total Synthesis ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
The Cross

The reactivity of novel α-hydroxy β,γ-unsaturated amides in cross-metathesis reactions was extensively studied and used to perform a short total synthesis of symbioramide and its isomer from ­l-serine methyl ester.

Synthesis of Unsaturated Esters by Cross-Metathesis of Terpenes and Natural Rubber Using Ru-Alkylidene Catalysts

2019 ◽  
Vol 23 (12) ◽  
pp. 1356-1364
Author(s):  
Araceli Martínez ◽  
Mikhail A. Tlenkopatchev ◽  
Selena Gutiérrez ◽  
Manuel Burelo ◽  
Joel Vargas ◽  
...  
Keyword(s):  
Natural Rubber ◽  
Unsaturated Ester ◽  
Low Molecular Weight ◽  
Diethyl Maleate ◽  
Metathesis Reaction ◽  
Unsaturated Esters ◽  
Cross Metathesis ◽  
Dimethyl Maleate ◽  
The Cross ◽  
Low Activity

This study reports the cross-metathesis of bicyclic &#946;-pinene, acyclic cis-3- methylpent-2-ene terpenes and the natural rubber with functionalized olefins, a route for the functionalization of the carbon-carbon double bond of natural products to obtain aliphatic unsaturated esters. The production of unsaturated esters from &#946;-pinene and cis-3- methylpent-2-ene via cross-metathesis reaction with dimethyl maleate and diethyl maleate in the presence of the ruthenium-alkylidene [Ru(Cl)2(=CHPh)(1,3-bis(2,4,6- trimethylphenyl)-2-imidazolidinylidene)(PCy3)] (I), [Ru(Cl)2(=CH(o-isopropoxyphenylmethylene))( 1,3-bis(2,4,6-trimethylphenyl) -2-imidazolidinylidene)] (II) and rutheniumvinylidene [RuCl2(=C=CH(p-C6H4CF3))(PCy3)2] (III) was carried out. Results showed that the reaction of &#946;-pinene with diethyl maleate using II catalyst produced unsaturated esters with 43 % selectivity. I and III catalysts showed low activity toward the cross-metathesis of &#946;-pinene and dimethyl maleate. A survey about the cross-metathesis of acyclic cis-3-methylpent-2-ene with diethyl maleate by II catalyst was also studied. The formation of ethyl but-2-enoate and ethyl-3-methylpent-2-enoate products was highly selective by 63 %. The unsaturated esters formation from the cross-metathesis degradation of natural rubber (99.9 % cis-polyisoprene) with dimethyl maleate and diethyl maleate using I-III catalysts was accomplished as well. I and II catalysts showed high activity in the degradation of natural rubber with diethyl maleate to produce the low molecular weight of oligomers unsaturated ester products (Mn = 1 x 103 g mol-1) with isoprene units of m = 10 – 27 and yields ranging from 68 to 94 %.

scholarly journals Fishing for the right catalyst for the cross-metathesis reaction of methyl oleate with 2-methyl-2-butene

2017 ◽  
Vol 7 (6) ◽  
pp. 1284-1296 ◽  
Author(s):  
A. Sytniczuk ◽  
A. Kajetanowicz ◽  
K. Grela
Keyword(s):  
Methyl Oleate ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross ◽  
The Right

A comparison of the reactivity of different ruthenium-based complexes in the cross-metathesis reaction of methyl oleate was presented.

Exploiting the cross-metathesis reaction in the synthesis of pseudo-oligosaccharides

2009 ◽  
Vol 7 (12) ◽  
pp. 2635 ◽  
Author(s):  
Paolo Ronchi ◽  
Stefano Vignando ◽  
Sara Guglieri ◽  
Laura Polito ◽  
Luigi Lay
Keyword(s):  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross
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