7540-51-4Relevant academic research and scientific papers
Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization
Kathe, Prasad M.,Berkefeld, Andreas,Fleischer, Ivana
supporting information, p. 1629 - 1632 (2021/02/09)
This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.
Total Syntheses of C60- And C100-Dolichols
Hirao, Kohtaro,Ono, Risako,Manabe, Yoshiyuki,Masui, Seiji,Atomi, Haruyuki,Fukase, Koichi
, p. 11549 - 11559 (2020/10/12)
C60- and C100-dolichols were synthesized. A Z-selective Wittig reaction was achieved with high selectivity in a microflow system to realize the scalable supply of the Z-isoprene unit. An isoprene chain was efficiently elongated by an SN2-type coupling between allyl sulfone and allyl chloride using t-BuOK. These key reactions enabled the efficient syntheses of dolichols. This study will pave the way for the functional studies of dolichols.
Asymmetric synthesis of γ-chiral borylalkanes: Via sequential reduction/hydroboration using a single copper catalyst
Han, Jung Tae,Lee, Jin Yong,Yun, Jaesook
, p. 8961 - 8965 (2020/11/23)
The synthesis of γ-chiral borylalkanes through copper-catalyzed enantioselective SN2′-reduction of γ,γ-disubstituted allylic substrates and subsequent hydroboration was reported. A copper-DTBM-Segphos catalyst produced a range of γ-chiral alkylboronates from easily accessible allylic acetate or benzoate with high enantioselectivities up to 99% ee. Furthermore, selective organic transformations of the resulting γ-chiral alkylboronates generated the corresponding γ-chiral alcohol, arene and amine compounds.
Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups
Fujiki, Katsumasa,Tanaka, Katsunori
supporting information, p. 4616 - 4620 (2020/07/06)
The first known report on the fluoride catalytic reactivity of potassium aryltrifluoroborate is described. The fluoride reactivity of phenyltrifluoroborate was controlled by substituents on the trifluoroborate-attached benzene, such as the methoxy group a
Method for synthesizing levorotatory citronellol by asymmetric hydrosilation of citral
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Paragraph 0010; 0049-0065, (2020/04/17)
The invention provides a method for synthesizing levorotatory citronellol from citral through asymmetric hydrosilation. The method comprises following steps: under the catalytic action of a chiral ruthenium complex, monohydrosilane is used as a hydrosilylation reagent, a Lewis acid is used as an auxiliary agent, and citral is subjected to asymmetric hydrosilylation to obtain levorotatory citronellol. According to the method, the ruthenium complex which is relatively low in price is used as the catalyst, meanwhile, the use amount of the ruthenium complex is effectively reduced, the maximum molar ratio of the chiral ruthenium complex to citral can reach 1: 30000, and the cost of the catalyst is remarkably reduced.
Enantioselective Synthesis and Activity of All Diastereoisomers of (E)-Phytal, a Pheromone Component of the Moroccan Locust, Dociostaurus maroccanus
Guerrero, Angel,Ramos, Victoria Elena,López, Sergio,Alvarez, José María,Domínguez, Aroa,Coca-Abia, María Milagro,Bosch, María Pilar,Quero, Carmen
, p. 72 - 80 (2019/01/15)
The Moroccan locust, Dociostaurus maroccanus (Thunberg, 1815) (Orthoptera: Acrididae), is a polyphagous pest capable of inflicting large losses in agriculture under favorable environmental and climatic conditions. Currently, control of the pest relies solely on the application of conventional insecticides that have negative effects on the environment and human safety. In the search for a more rational, environmentally acceptable approach for locust control, we have previously reported that (Z/E)-phytal (1) is a male-produced candidate sex pheromone of this acridid. This molecule, with two stereogenic centers at C-7 and C-11, has four different diastereomers along with the Z/E stereochemistry of the double bond at C-2. In this paper, we present for the first time the enantioselective synthesis of the four diastereomers of (E)-phytal and their electrophysiological and behavioral activity on males and females. Our results demonstrate that the (R,R)-phytal is the most active diastereomer in both assays, significantly attracting females in a double-choice Y olfactometer, and confirming the previous chromatographic assignment as component of the sex pheromone of the Moroccan locust.
Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations
Funk, Timothy W.,Mahoney, Andrew R.,Sponenburg, Rebecca A.,Zimmerman, Kathryn P.,Kim, Daniel K.,Harrison, Emily E.
supporting information, p. 1133 - 1140 (2018/04/17)
Four (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds were synthesized, and their activities in transfer hydrogenations of carbonyl compounds and transfer dehydrogenations of alcohols were explored and compared to those of the well-established [2,5-(SiMe3)2-3,4-(CH2)4(η4-C4C=O)]Fe(CO)3 (3). A new compound, [2,5-bis(3,5-dimethylphenyl)-3,4-diphenylcyclopentadienone]iron tricarbonyl (7), was the most active catalyst in both transfer hydrogenations and dehydrogenations, and compound 3 was the least active catalyst in transfer hydrogenations. Evidence was found for product inhibition of both 3 and 7 in a transfer dehydrogenation reaction, with the activity of 3 being more heavily affected. A monomeric iron hydride derived from 7 was spectroscopically observed during a transfer hydrogenation, and no diiron bridging hydrides were found under reductive or oxidative conditions. Initial results in the transfer hydrogenation of N-benzylideneaniline showed that 3 was a significantly less active catalyst in comparison to the (3,4-diphenylcyclopentadienone)iron tricarbonyl compounds.
Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities
Mori, Kenji,Akasaka, Kazuaki
, p. 182 - 187 (2018/10/16)
The enantiomers of citronellal have been converted into the enantiomers of the following beetle pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-1-carboxylic acid].
Method for preparing chiral citronellol through asymmetric catalytic hydrogenation of citral
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Paragraph 0137-0138, (2017/01/26)
The invention relates to a method for preparing single chiral citronellol through asymmetric catalytic hydrogenation of E-type and/or Z-type citral in the technical field of chemical engineering. The method comprises the step of performing asymmetric hydrogenation on the E-type and/or Z-type citral to form single chiral citronellol under certain hydrogen pressure and at a certain temperature under the catalysis of a chiral rhodium complex. The reaction condition is mild, the method is convenient to operate, the reaction efficiency is higher, the product yield and the enantioselectivity can reach 99%, and the method has bright industrial application prospect.
Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes
Verma, Ajay,Jana, Sadhan,Prasad, Ch. Durga,Yadav, Abhimanyu,Kumar, Sangit
supporting information, p. 4179 - 4182 (2016/03/19)
A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.
