79618-90-9Relevant academic research and scientific papers
S,O-Ligand-Promoted Pd-Catalyzed C?H Olefination of Anisole Derivatives
Fernández-Ibá?ez, M. ángeles,Jia, Wen-Liang,Sukowski, Verena,van Borselen, Manuela,van Diest, Rianne
supporting information, p. 4132 - 4135 (2021/08/24)
The C?H olefination of substituted anisole derivatives by a Pd/S,O-ligand catalyst is reported. The reaction proceeds under mild conditions with a broad range of substituted aryl ethers bearing both electron donating and withdrawing substituents at ortho,
Synthesis and evaluation of the bioactivity of simplified analogs of the seco-pseudopterosins; progress toward determining a pharmacophore
Tanis, Virginia M.,Moya, Claudia,Jacobs,Little, R. Daniel
, p. 10649 - 10663 (2008/12/23)
The pseudopterosins are marine natural products that display significant anti-inflammatory and wound healing properties. We describe the synthesis of six structural analogs of the seco-pseudopterosin-like core that are devoid of all but one of the stereoc
Pd(OAc)2-Catalyzed Oxidative Coupling Reaction of Benzenes with Olefins in the Presence of Molybdovanadophosphoric Acid under Atmospheric Dioxygen and Air
Tani, Masayuki,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 1221 - 1226 (2007/10/03)
The direct oxidative coupling reaction of benzenes with alkenes bearing an electron-withdrawing group was successfully achieved by the use of Pd(OAc) 2/molybdovanadophosphoric acid (HPMoV) as the key catalyst under O2 or air atmosphere. Thus, the reaction of benzene with ethyl acrylate under air (1 atm) assisted by Pd(OAc)2/HPMoV afforded ethyl cinnamate as a major product in satisfactory yield (74%). This catalytic system could be extended to the coupling reactions between various substituted benzenes and alkenes through the direct aromatic C-H bond activation. In the reaction of benzene with ethyl acrylate under O2 (1 atm), the best turn-over number (TON) of Pd(OAc)2 reached was 121. This reaction provides a green route to cinnamate derivatives, which are important precursors of a variety of pharmaceuticals.
Iron tricarbonyl stabilized pentadienyl cation as initiator for cascade polycyclizations: A diastereoselective entry into octahydrophenanthrenes
Pearson, Anthony J.,Ghidu, Victor P.
, p. 8975 - 8978 (2007/10/03)
A new example is provided of completely diastereoselective polycyclization, affording the octahydrophenanthrene framework. Generation of an iron tricarbonyl stabilized pentadienyl carbocation is the triggering event of the cascade reaction. The carbocation is generated by anchimerically assisted regiospecific protonation of a double bond adjacent to the iron tricarbonyl diene moiety. Tetrafluoroboric acid ether complex appears to be the optimum reagent, affording good yields, even under catalytic conditions.
Synthesis of linear alkyl-bridged 2,2'-bipyridine/catechol ligands
Albrecht, Markus,Riether, Cyrill
, p. 957 - 962 (2007/10/03)
Linear alkyl-bridged 2,2'-bipyridine/catechol compounds [1,12-14, 19]-H2 and [2,20]-H4 can be easily prepared by the addition of lithiated 5,5'-methyl-2,2'-bipyridine (3) to 3-(ω-haloalkyl)-substituted 1,2-dimethoxybenzenes 4, 9, 11,
Codeine Analogues. Synthesis of Spiro and Octahydro-1H-benzofuroisoquinolines
Moos, Walter H.,Gless, Richard D.,Rapoport, Henry
, p. 5064 - 5074 (2007/10/02)
A synthesis of highly functionalized spiro and octahydro-1H-benzofuroisoquinolines, analogues of codeine containing the benzofuran/piperidine and benzofuran/decahydroisoquinoline ring fragments, has been developed.The process extends to the dimethoxyphenyl series earlier work in the synthesis of 4a-aryldecahydroisoquinolines involving the α-methylene lactam rearrangement and utilizes a novel α-chloro ortho ester Claisen rearrangement to establish the requisite functionality for oxide ring closure.Selective ether cleavage is achieved with methanesulfonic acid/methionine to afford a spiro, and base-promoted rearrangement then yields the desired spiro.The C-ring is closed by Michael addition of a β-keto ester to the α-methylene lactam moiety, subsequently affording a protected benzofuroisoquinolone.Finally, amide reduction followed by ketone deprotection gives the desired cis- and trans-benzofuroisoquinolines.The entire synthesis can be performed by starting from o-vanillin with six purifications in 10percent overall yield, and the various intermediates additionally provide entries into the synthesis of 4-arylpiperidines, benzomorphans, and 4a-aryldecahydroisoquinolines.Functionality is built in to allow preparation of typical morphine patterns.
Substituent Effects in the Reaction of t-Butylmagnesium Chloride with Substituted Ethyl Cinnamates. A Correlation with 13C NMR Chemical Shifts
Jalander, Lars
, p. 419 - 428 (2007/10/02)
The reaction of t-butylmagnesium chloride with some substituted ethyl (E)-cinnamates gave mainly 1,3-, 1,4-, 1,2- and 1,4-addition products and minor amounts of 1,2- and 1,3-addition products.The relative amounts of 1,3-addition products has been shown to correlate with 13C NMR chemical shifts of C-α of the ethyl cinnamates.The correlation indicates that the regio selectivity of the reactions is to a great extent dependent of polar effects and that the t-butyl radical has a nucleophilic character.
