1205-17-0Relevant articles and documents
Hydroformylation of natural olefins with the [Rh(COD)(μ-OMe)]2/TPPTS complex in BMI-BF4/toluene biphasic medium: Observations on the interfacial role of CTAB in reactive systems
Baricelli, Pablo J.,Borusiak, Margarita,Crespo, Isis,Melean, Luis G.,Pereira, Juan C.,Rodríguez, Mariandry,Rosales, Merlín
, (2020)
The complex [Rh(COD)(μ-OMe)]2 in presence of TPPTS (TPPTS = triphenylphosphinetrisulfonate) was evaluated as catalyst precursor for the in situ hydroformylation of natural olefins (eugenol, estragole and safrole) in biphasic media BMIm-BF4/toluene. Under moderate reaction conditions, the substrates showed the following reactivity order: eugenol > estragole > safrole. The rhodium system showed a high activity and selectivity towards the desired aldehydes. It was found that the use of cetyltrimethylammoniun bromide (CTAB) as phase transfer agent inhibits the hydroformylation reaction. The catalytic phase can be recycled up to four times without evident loss of activity or selectivity. In this work we report the use of an ionic liquid with hydrophilic character, without using water in the reaction medium.
Bioreduction of α-methylcinnamaldehyde derivatives: Chemo-enzymatic asymmetric synthesis of Lilial and Helional
Stueckler, Clemens,Mueller, Nicole J.,Winkler, Christoph K.,Glueck, Silvia M.,Gruber, Karl,Steinkellner, Georg,Faber, Kurt
, p. 8472 - 8476 (2010)
Nonracemic aryl-substituted α-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial, Helional) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e. max 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1-3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of α-methylcinnamaldehyde using NCR and OYEs 1-3 [previously reported to be (R)] was unambiguously corrected to be (S).
Synthesis method of helional
-
Paragraph 0018; 0035-0050, (2021/10/16)
The invention relates to a synthesis method of helional, and belongs to the technical field of organic synthesis. According to the synthesis method of helional, the method comprises the following step: at the reaction temperature of 60-80 DEG C, in a reaction kettle provided with rising microbubbles, carrying out catalytic reaction by taking methylacrolein and benzodioxole as raw materials and taking Bronsted acid as a catalyst to synthesize the helional in one step. The chemical reaction formula is shown in the specification. The synthesis method of the helional can be carried out under low pressure or normal pressure. In the method, inert gas and gaseous methylacrolein are mixed according to a specific proportion, and the mixed gas is pumped into a reactor filled with benzodioxole through the reinforced microbubble reactor, so that methylacrolein and benzodioxole react quickly, and side reaction caused by unstable methylacrolein is avoided. In the conventional method, methylacrolein needs to react with acetic anhydride for protection, and then react with benzodioxole for deprotection, and thus chemical wastes are generated.
Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis
Su, Yong-Liang,Li, Lu-Lu,Zhou, Xiao-Le,Dai, Zhen-Yao,Wang, Pu-Sheng,Gong, Liu-Zhu
, p. 2403 - 2406 (2018/04/27)
A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.