36597-08-7Relevant academic research and scientific papers
Catalytic addition-cyclization of alkyl ketones with 4-methyl-1-phenyl-4-penten-1-one
Ipatkin,Kovalev,Ignatenko,Nikishin
, p. 7971 - 7972 (1993)
Substituted 2-(β-oxoalkyl)tetrahydrofurans were obtained in one-step aldol-type reaction from alkyl ketones and 4-methyl-1-phenyl-4-penten-1-one in the presence of a catalytic system [RhCl(C2H4)2]2-SnCl2/s
KOtBu/DMSO Catalytic System for Isomerization of Allylic Alcohols to Ketones
Sai, Masahiro
supporting information, (2022/04/03)
The isomerization of allylic alcohols is an important reaction because it can afford carbonyl compounds in an atom-economical manner. Although base-catalyzed methods are more desirable than those using transition-metal catalysts from both the economic and environmental points of view, these methods have several drawbacks, such as narrow substrate scope and high catalyst loading. This paper reports the development of an efficient KOtBu/DMSO catalytic system suitable for the isomerization of a broad range of allylic alcohols with good yields, to which previously reported systems could not be applied. This catalytic system was successfully applied to a tandem allylic isomerization/electrophilic trapping reaction, thereby highlighting its synthetic utility.
Sc(OTf)3a'Catalyzed Ca'C Bond-Forming Reaction of Cyclic Peroxy Ketals for the Synthesis of Highly Functionalized 1,2-Dioxene Endoperoxides
Feng, Haowei,Zhao, Yukun,Liu, Pengkang,Hu, Lin
supporting information, p. 1632 - 1637 (2021/03/08)
A new and general Sc(OTf)3-catalyzed C-C bond-forming reaction of 3-(2-methoxyethoxy)-endoperoxy ketals with silyl ketene acetals, silyl enol ethers, allyltrimethylsilane, and trimethylsilyl cyanide has been developed via the reactive peroxycarbenium ions, affording a wide range of complicated 3,3,6,6-tetrasubstituted 1,2-dioxenes bearing adjacent quaternary carbons and 3-acetyl/allyl/cyano functional groups in good yields at room temperature. Notably, the resultant 1,2-dioxenes are structurally stable, which can be facially transformed into another important 1,2-dioxane endoperoxide under conventional hydrogenation conditions without deconstructing the weak O-O bond.
Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones
Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Pan, Chenjing,Su, Zhishan,Wu, Zhikun,Zhang, Dong,Zhou, Yuqiao
supporting information, p. 15975 - 15985 (2020/10/18)
Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- A nd enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N′-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearomatic oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds. More importantly, the stereochemistry of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochemistry during the reaction processes.
Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis
Erkman, Kristin,J?rving, Ivar,K?ster, Kristjan,Kanger, T?nis,Leito, Ivo,Mart?nova, Jevgenija,Metsala, Andrus,Saame, Jaan,Trubits?n, Dmitri
, p. 1047 - 1059 (2020/04/01)
An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones
Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.
, p. 197 - 200 (2018/12/13)
The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.
Enantioselective Conjugate Azidation of α,β-Unsaturated Ketones under Bifunctional Organocatalysis by Direct Activation of TMSN3
Humbrías-Martín, Jorge,Pérez-Aguilar, M. Carmen,Mas-Ballesté, Rubén,Dentoni Litta, Antonella,Lattanzi, Alessandra,Della Sala, Giorgio,Fernández-Salas, Jose A.,Alemán, José
supporting information, p. 4790 - 4796 (2019/09/16)
An enantioselective organocatalytic conjugate azidation of α,β-unsaturated ketones is presented. A bifunctional organocatalyst activates TMSN3, triggering the nucleophilic addition of the azido group to enones in absence of external promoters and avoiding the direct use or the pre-formation of highly toxic and explosive hydrazoic acid. This protocol proceeds with excellent enantiocontrol under mild conditions. DFT calculations and mechanistic trials have been performed in order to demonstrate the direct activation performed by the bifunctional organocatalyst. (Figure presented.).
Barluenga's reagent with HBF4 as an efficient catalyst for alkyne-carbonyl metathesis of unactivated alkynes
Murai, Kosuke,Tateishi, Keiichiro,Saito, Akio
supporting information, p. 10352 - 10356 (2016/11/18)
Barluenga's reagent (IPy2BF4, Py = pyridine) treated with HBF4 efficiently catalyzes the inter- and intramolecular alkyne-carbonyl metathesis of unactivated alkynes with aldehydes or ketones, most of which proceed at room temperature. This work represents the first catalytic application of the Barluenga's reagent.
1,5-dicarbonyl derivative and preparation method thereof
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Paragraph 0045, (2016/10/07)
The invention provides a synthesis method of a 1,5-dicarbonyl compound. According to the method, under the conditions of employing triethylamine as alkali, an ionic liquid [BMIM] PF6 as a solvent and lithium tetrafluoroborate as an adjuvant, a series of n
A convenient synthesis of 4-alkyl-3-benzoylpyrroles from α,β-unsaturated ketones and tosylmethyl isocyanide
Kumar, Kapil,More, Shital S.,Goyal, Sandeep,Gangar, Mukesh,Khatik, Gopal L.,Rawal, Ravindra K.,Nair, Vipin A.
, p. 2315 - 2319 (2016/05/10)
A convenient synthesis of 4-alkyl-3-benzoyl pyrrole was achieved from α,β-unsaturated ketones and tosylmethyl isocyanide in the presence of mild base LiOH·H2O. This method is very economical and was successfully utilized for the synthesis of various 4-alkyl-3-benzoylpyrrole derivatives with good to excellent yields.
