53329-00-3Relevant academic research and scientific papers
Synthesis of Short-Chain Alkenyl Ethers from Primary and Bio-sourced Alcohols via the Nickel-Catalyzed Hydroalkoxylation Reaction of Butadiene and Derivatives
Mifleur, Alexis,Ledru, Hlne,Lopes, Adrien,Suisse, Isabelle,Mortreux, Andr,Sauthier, Mathieu
, p. 110 - 121 (2016/01/25)
Hydroalkoxylation of butadiene has been performed in the presence of nickel precatalysts associated with chelating diphosphine ligands. High butadiene conversions and selectivities forming alkyl butenyl ethers were obtained with low catalyst loading. Reactions were performed with a wide scope of primary alcohols including benzylic alcohol derivatives and bio-sourced alcohols. In the same way, the scope of dienes that can be reacted according to this reaction has been also studied. Substituted butadiene derivatives have shown a lower reactivity compared to butadiene. Isoprene formed OC5 alkenyl ethers with a high regioselectivity for one branched isomeric form.
Hydrogen-bond-activated palladium-catalyzed allylic alkylation via allylic alkyl ethers: Challenging leaving groups
Huo, Xiaohong,Quan, Mao,Yang, Guoqiang,Zhao, Xiaohu,Liu, Delong,Liu, Yangang,Zhang, Wanbin
supporting information, p. 1570 - 1573 (2014/04/17)
C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).
Nickel-catalysed hydroalkoxylation reaction of 1,3-butadiene: Ligand controlled selectivity for the efficient and atom-economical synthesis of alkylbutenyl ethers
Bigot, Sandra,El Alami, Mohammed Samir Ibn,Mifleur, Alexis,Castanet, Yves,Suisse, Isabelle,Mortreux, Andre,Sauthier, Mathieu
, p. 9785 - 9788 (2013/08/23)
The nickel-catalysed hydroalkoxylation of butadiene is promoted by a nickel(0)/dppb catalyst (dppb=1,4-bis(diphenylphosphino)butane; see scheme). By following this new synthetic procedure, alkylbutenyl ethers are readily obtained from an alcohol and 1,3-butadiene with exclusion of dimerisation and telomerisation products. Copyright
The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information, p. 3437 - 3444 (2013/07/05)
A 1:1 mixture of [AuCl(IPr)] (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidine) and AgClO4 catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to for
Synthesis of N-protected allylic amines from allyl ethers
Kim, Ji Duck,Lee, Min Hee,Han, Gyoonhee,Park, Hyunju,Zee, Ok Pyo,Jung, Young Hoon
, p. 8257 - 8266 (2007/10/03)
A synthetic method for N-protected allylic amines from allyl ethers using chlorosulfonyl isocyanate (CSI) is presented. The reaction of 4-phenylbut-2-enyl methyl ether (1i) with CSI afforded methyl N-(1-benzylallyl)carbamate (2i) and methyl N-(4-phenylbut
Synthesis of Analogues of 1,3-Dihydroxyacetone Phosphate and Glyceraldehyde 3-Phosphate for Use in Studies of Fructose-1,6-diphosphate Aldolase
Bischofberger, Norbert,Waldmann, Herbert,Saito, Tohru,Simon, Ethan S.,Lees, Watson,et al.
, p. 3457 - 3465 (2007/10/02)
This paper describes the synthesis of five analogues of dihydroxyacetone phosphate (3-azidohydroxyacetone 1-phosphate (5), 3-(acetylamino)hydroxyacetone 1-phosphate (12), (R)-1,3-dihydroxy-2-butanone 1-phosphate (18), (+/-)-1,3-dihydroxy-2-butanone 3-phosphate (26), and phosphonomethyl glycolate (31)).The syntheses of 18 and 26 are based on a new reaction: that is, the introduction of the phosphate group by the reaction of a diazo ketone with dibenzyl phosphate.These methods provide easy access to a number of compounds that are potential substrates for the synthetically useful enzyme aldolase (fructose-1,6-diphosphate aldolase from rabbit muscle, EC 4.1.2.13, RAMA) and perhaps for other enzymes of glycolysis.This paper also describes syntheses of 14 aldehydes for examination as substrates for aldolase.When the precursor was available, ozonolysis of vinyl groups proved to be the best route to the corresponding aldehydes.
PREPARATION AND SYNTHETIC UTILIZATION OF 3-(ADENIN-9-YL)-2-HYDROXYALKANOIC ACIDS AND THEIR DERIVATIVES
Holy, Antonin
, p. 2148 - 2166 (2007/10/02)
Condensation of adenine and its substituted derivatives with 1,1-dialkoxy-2-bromoalkanes afforded substituted 2-(adenin-9-yl)-1,1-dialkoxyalkanes I and IV.Acid hydrolysis of I or IV, followed by reaction with alkali metal cyanides and acid hydrolysis, gave substituted 3-(adenin-9-yl)-2-hydroxyalkanoic acids II, V and VI.Methyl esters of these compounds (VIII) were converted into 3-(adenin-9-yl)alkane-1,2-diols IX by reduction with sodium borohydride. 3-(Adenin-9-yl)-2-methoxypropanoic acid (XVII) was obtained by oxidation of 9-(3-hydroxy-2-methoxypropyl)adenine (XVI)with sodium periodate; 4-(adenin-9-yl)-2-(S)-hydroxybutanoic acid (XXVII) was synthesized by oxidation of 9-(S)-(2-tetrahydropyranyloxy-4-hydroxybutyl)adenine (XXV), prepared from diethyl L-malate.Acid hydrolysis of XXV afforded 9-(S)-(2,4-dihydroxybutyl)adenine (XXVI). 4-(Adenin-9-yl)-3-hydroxypentanoic acid (XXIX) was obtained by reaction of malonic acid with 2-(adenin-9-yl)-1,1-diethoxypropane (IVa) in water.
