65825-74-3Relevant academic research and scientific papers
Oxidative conversion of silyl enol ethers to α,β-unsaturated ketones employing oxoammonium salts
Hayashi, Masaki,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
, p. 154 - 157 (2012/02/16)
The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO +BF4-) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.
Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C
Felpin, Francois-Xavier
, p. 8575 - 8578 (2007/10/03)
The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(0)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 °C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(0)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.
Organic synthesis in ionic liquids: The stille coupling
Handy, Scott T.,Zhang, Xiaolei
, p. 233 - 236 (2007/10/03)
equation presented The Stille coupling reaction has been performed in 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM BF4), a room-temperature ionic liquid (RTIL). Use of this solvent system allows for facile recycling of the solvent and catalyst system, which can be used at least five times with little loss in activity. An interesting preference in starting catalyst oxidation state for use with aryl bromides and aryl iodides was observed.
Synthesis of 2-phenyl-2-cycloalkenones via palladium-catalyzed tandem epoxide isomerization-intramolecular aldol condensation
Kim, Ji-Hyun,Kulawiec, Robert J.
, p. 3107 - 3110 (2007/10/03)
We have extended the scope of our palladium-catalyzed tandem epoxide isomerization/aldol condensation reaction to encompass intramolecular condensations, which provide facile access to conjugated cycloalkenones from epoxy aldehydes or diepoxides. For example, reaction of 5,6-epoxy-6- phenylhexanal with Pd(OAc)2-PBu3 catalyst in the presence of NaHCO3 and 3A molecular sieves forms 2-phenyl-2-cyclopentenone (80%). Similarly, 1,2;5,6-diepoxy-1-phenylhexane affords 3-methyl-2-phenyl-2-cyclopentenone (72%). The observation of dicarbonyl intermediates (e.g., 1-phenyl-2,5- hexanedione in the latter case) demonstrates that the reaction proceeds via Pd-catalyzed isomerization of the diepoxide to the diketone, followed by base-catalyzed aldol condensation.
The Reaction of 2-Substituted Cycloalkanones with Aldehydes under Acidic Conditions
Sato, Tadashi,Hayase, Kengo
, p. 3384 - 3389 (2007/10/02)
The title reaction proceeded with either ring enlargement or bicyclic compound formation, as well as the aldol reaction, depending upon the types of the reactants and reaction conditions.
Strategic Synthesis based on Cyclohexadienes: Preparation of 2-, 2,3- and 2,4-Substituted Cyclohexenones; Synthesis of (Z)-Heneicosa-6-en-11-one
Pramod, Kakumanu,Ramanathan, Halasya,Rao, G. S. R. Subba
, p. 7 - 10 (2007/10/02)
The mesomeric anions, generated from 1-methoxycyclohexa-1,4-diene, 1-methoxy-5-methylcyclohexa-1,4-diene, and 1-methoxy-4-methylcyclohexa-1,4-diene with potassium amide in liquid ammonia, have been readily alkylated and the resulting dienes were hydrolysed to yield 2-alkyl-, 2,3-dialkyl- and 2,4-dialkyl-cyclohex-2-enones in good yield.Arylation of the above mesomeric anions followed by hydrolysis afforded 2-arylcyclohex-2-enones in addition to substituted biphenyls.A new and efficient synthesis of the male sex attractant of the Douglas Fir Tussock Moth, (Z)-heneicosa-6-en-11-one is described using the above methodology.
