38019-50-0Relevant academic research and scientific papers
Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic enones
Kim, Jeung Gon,Waltz, Karen M.,Garcia, Iliana F.,Kwiatkowski, David,Walsh, Patrick J.
, p. 12580 - 12585 (2004)
A simple procedure is reported for the catalytic asymmetric allylation of ketones, utilizing titanium tetraisopropoxide, BINOL, 2-propanol additive, and tetraallylstannane as allylating agent. A variety of ketone substrates, including acetophenone derivat
Hydroxy chalcogenide-promoted Morita-Baylis-Hillman Alkylation reaction: Intermolecular applications with alkyl halides as electrophiles
Gradillas, Ana,Belmonte, Efres,Da Silva, Rondes Ferreira,Perez-Castells, Javier
, p. 1935 - 1941 (2014/04/03)
Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the MBH alkylation, but fine-tuning the reaction conditions minimized their occurence.
Hydroxy Chalcogenide-Promoted Morita-Baylis-Hillman Alkylation Reaction: Intermolecular Applications with Alkyl Halides as Electrophiles
Gradillas, Ana,Belmonte, Efres,Da Silva, Rondes Ferreira,Prez-Castells, Javier
, p. 1935 - 1941 (2015/10/05)
Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the
An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues
Yu, Binxun,Jiang, Tuo,Quan, Weiguo,Li, Junpeng,Pan, Xinfu,She, Xuegong
supporting information; experimental part, p. 629 - 632 (2009/07/25)
(Chemical Equation Presented) The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the
METHOD FOR MAKING BIARYL COMPOUNDS, COMPOUNDS MADE BY THE METHOD, AND METHOD FOR THEIR USE
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Page/Page column 91-92, (2009/01/23)
Certain disclosed embodiments of the present invention concern a method for making biaryl compounds by combining a diene with a dienophile under reaction conditions that facilitate a Diels-Alder reaction. Certain embodiments are particularly directed to making a tetra-ortho-substituted biaryl compounds. The disclosed method may involve using novel dienes, dienophiles, or both. Similarly, certain of the biaryl compounds are novel compounds too. Additional disclosed embodiments concern a method for making useful compounds by first making a Diels-Alder adduct. The Diels-Alder adduct is then further modified or coupled to other compounds. The method can be used to make carbazoles, such as Siamenol. Disclosed biaryl compounds are useful for a number of applications, such as pharmacophores and organocatalysts.
Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine
Trost, Barry M.,Tang, Weiping,Toste, F. Dean
, p. 14785 - 14803 (2007/10/03)
An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.
Tetrathiafulvalene-mediated stereoselective synthesis of the tetracyclic core of Aspidosperma alkaloids
Fletcher, Rodney,Kizil, Murat,Lampard, Christopher,Murphy, John A.,Roome, Stephen J.
, p. 2341 - 2351 (2007/10/03)
A novel route to advanced synthetic precursors of Aspidosperma alkaloids is described, utilising radical-polar crossover reactions.
Mn(III)-based oxidative free-radical cyclizations of unsaturated ketones
McCarthy Cole, Bridget,Han, Luning,Snider, Barry B.
, p. 7832 - 7847 (2007/10/03)
Mn(III)-based oxidative free-radical cyclization of unsaturated ketones is a versatile synthetic procedure with broad applicability. For example, oxidation of cyclopentanone 1a with 2 equiv of Mn(OAc)3·2H2O and 1 equiv of Cu(OAc)sub
Stereocontrolled synthesis of complex polycycles using tetrathiafulvalene mediated radical-polar crossover reactions
Fletcher, Rodney J.,Hibbs,Hursthouse,Lampard, Christopher,Murphy, John A.,Roome, Stephen J.
, p. 739 - 740 (2007/10/03)
Tetracyclic heterocycles are prepared in a stereocontrolled manner using radical-polar crossover chemistry.
