57428-66-7Relevant academic research and scientific papers
Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents
Lee, Kooyeon,Kim, Hyunseok,Mo, Juntae,Lee, Phil Ho
scheme or table, p. 2147 - 2157 (2011/10/31)
Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions, using allylindium generated in situ from allyl halides and indium, is demonstrated. Allylindium compounds may be effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions. A variety of allyl halides, such as allyl iodide, allyl bromide, crotyl bromide, prenyl bromide, geranyl bromide, and 3-bromocyclohexene afforded the allylic cross-coupling products in good to excellent yields. Stereochemistry of the double bond is retained in the allylic cross-coupling reactions. Electrophilic cross-coupling partners, such as aryl and vinyl halides, dibromoolefin, alkynyl iodide, and aryl and vinyl triflates participate in these reactions. The presence of various substituents, such as n-butyl, ketal, acetyl, ethoxycarbonyl, nitrile, N-phenylamido, nitro, and chloride groups on the aromatic ring of electrophilic coupling partners showed little effect on the efficiency of the reactions. The present conditions work equally well for not only intermolecular but also intramolecular palladium-catalyzed cross-coupling reactions. These methods provide an efficient synthetic method for the introduction of an allyl group, which can be easily further functionalized to afford an sp2- and sp-hybridized carbon. The present method complements existing synthetic methods as a result of advantageous features such as easy preparation and handling, thermal stability, high reactivity and selectivity, operational simplicity, and low toxicity of allylindium reagents.
Development of a strategy for the asymmetric synthesis of polycyclic polyprenylated acylphloroglucinols via N-amino cyclic carbamate hydrazones: Application to the total synthesis of (+)-clusianone
Garnsey, Michelle R.,Lim, Daniel,Yost, Julianne M.,Coltart, Don M.
scheme or table, p. 5234 - 5237 (2011/02/23)
A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated acylphloroglucinols is de
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
-
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.
2-CYANO-6-METHOXYTETRAHYDROPYRAN, A USEFUL PROTECTED CYANOHYDRIN FOR 2-SUBSTITUTED CYCLOHEXENONE SYNTHESIS
Laredo, Georgina Cecilia,Maldonado, Luis Angel
, p. 179 - 182 (2007/10/02)
The title compound 1, easily prepared from commercially available glutaraldehyde, is a protected cyanohydrin useful as synthon for the preparation of 2-substituted cyclohexenones.
Intramolecular Photochemical Reactions of 2-Acyl-1,5-hexadienes
Wolff, Steven,Agosta, William C.
, p. 1299 - 1304 (2007/10/02)
Photolysis of the 2-acyl-1,5-hexadienes 6-11 (Table I) leads to regiospecific crossed cyclization, yielding derivatives of bicyclohexane.Unlike dienones of the related classes 1 and 2, neither substitution at C(5) nor the presence of a ring influen
