91897-73-3Relevant articles and documents
Synthesis of cis-2,6-tetrahydropyran-4-one via diastereoselectively intramolecular cyclization of β-hydroxy allyl ketone
Lee, Adam Shih-Yuan,Lin, Li-Shin,Chang, Yu-Ting
, p. 3915 - 3919 (2012/07/14)
A series of cis-2,6-tetrahydropyran-4-ones was synthesized from the intramolecular cyclization reaction of β-hydroxy allyl ketones in the presence of Me3SiOTf as catalyst. The β-hydroxy allyl ketone was prepared from allylation reaction with β-hydroxynitrile without protection of hydroxy functionality under the Barbier-type reaction condition.
Stereoselective synthesis of cyclohexanones via phase transfer catalyzed double addition of nucleophiles to divinyl ketones
Silvanus, Andrew C.,Groombridge, Benjamin J.,Andrews, Benjamin I.,Kociok-Koehn, Gabriele,Carbery, David R.
supporting information; experimental part, p. 7491 - 7493 (2010/12/30)
Functionalized cyclohexanones are formed in excellent yield and diastereoselectivity from a phase transfer catalyzed double addition of active methylene pronucleophiles to nonsymmetrical divinyl ketones.
Stereoselective double friedel-crafts alkylation of indoles with divinyl ketones
Silvanus, Andrew C.,Heffernan, Stephen J.,Liptrot, David J.,Kociok-Koehn, Gabriele,Andrews, Benjamin I.,Carbery, David R.
supporting information; experimental part, p. 1175 - 1178 (2009/08/07)
A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic indoles in excellent yields. The reaction is completely regioselective and offers high levels of s
Study of the reaction of 1,1-bis(trimethylsilyl)-2-phenylethylene with some acyl chlorides in the presence of AlCl3
Safa, Kazem D.,Samani, Soleiman Paymard,Tofangdarzadeh, Shahin,Hassanpour, Akbar
, p. 2004 - 2008 (2008/09/19)
1,1-Bis(trimethylsilyl)-2-phenylethylene (1), which has been synthesized from the Peterson reaction between (Me3Si)3CLi and benzaldehyde, reacts with various acyl chlorides (RCOCl, R = Me, Et, iso-Pr, n-Bu, iso-Bu, iso-C5H11, PhCH2, PhCH2CH2) in the presence of AlCl3 to give α-silyl-α,β-unsaturated enones 3a-3h with high E stereoselectivity along with trans-α,β-unsaturated ketones 4a-4h. The enones 3 can be partially converted into the ketones 4 with an excess of AlCl3. Reaction of 1 with RCOCl, (R = Ph, CH3CH=CH) afforded only the ketones 4. Yields were dependent on time and the amounts of AlCl3 used.
Asymmetric Ni-catalyzed conjugate allylation of activated enones
Sieber, Joshua D.,Morken, James P.
, p. 4978 - 4983 (2008/09/20)
The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The rea
Catalytic conjugate addition of allyl groups to styryl-activated enones
Sieber, Joshua D.,Liu, Shubin,Morken, James P.
, p. 2214 - 2215 (2007/10/03)
Conjugate addition of pinacolato(allyl)boron to benzylidenealkylidene ketones is remarkably facile when catalyzed by Ni(0) and Pd(0) complexes. Simple enones are inert to the reaction conditions, suggesting a significant activating effect by the auxiliary benzylidene unit. A comparison of different catalysts and substrates is provided, as is a mechanistic rationale, and an example of asymmetric catalysis. Copyright
Combined computational and experimental studies of the mechanism and scope of the retro-Nazarov reaction
Harmata, Michael,Schreiner, Peter R.,Lee, Dong Reyoul,Kirchhoefer, Patrick L.
, p. 10954 - 10957 (2007/10/03)
Density functional theory calculations (B3LYP/6-31+G*) demonstrate that conjugating and electron-donating substituents at carbons three and four of a cyclopentenyl oxyallylic cation should have a rate-accelerating effect on the retro-Nazarov reactions of these species. The retro-Nazarov reaction of these intermediates is predicted to exhibit significant torquoselectivity when carbon three is substituted with a methoxy and a methyl group. Experimental studies show that oxyallylic cations can undergo effective retro-Nazarov reactions when two alkyl and one aryl/vinyl groups are on carbons three and four. An equal number of alkyl substituents or a single aryl substituent is not effective in promoting the reaction. Interestingly, a single alkoxy substituent at carbon three is sufficient for the retro-Nazarov reaction to occur. The methodology developed was used in a total synthesis of the natural product turmerone.
Catalytic asymmetric allylations of achiral and chiral aldehydes via BINOL-Zr complex
Kurosu, Michio,Lorca, Miguel
, p. 1765 - 1769 (2007/10/03)
The complex generated from BINOL, Zr(OtBu)4, and 4 ? MS in toluene-pivalonitrile is very effective for catalytic asymmetric allylation of aldehydes using allyltributyltin. The reactions of achiral aldehyde under these conditions are completed within 3 h using 10-20 mol% of the complex at -20°C. The ees of homoallylic alcohols can be enhanced up to 98% via the tandem asymmetric allylation-Oppenauer oxidations. The scope and limitations of these conditions for β-alkoxy aldehydes were extensively examined.
Carbometalation of cyclopropenes. Stereoselective synthesis of divinyl ketones via 1,5-hydrogen migration reaction of vinylcyclopropanes
Kubota, Katsumi,Isaka, Masahiko,Nakamura, Eiichi
, p. 565 - 574 (2007/10/03)
Stereoselective addition of a vinyl cuprate reagent to a cyclopropenone acetal (2) followed by in situ electrophilic trapping with an alkylating agent affords a cis-1-alkyl-2-vinylcyclopropanone acetal (3), which then undergoes thermal 1,5-hydrogen migrat
Carbometalation of Cyclopropenes. Stereoselective Synthesis of Divinyl Ketone Acetals by 1,5-Hydrogen Migration of Vinylcyclopropanes
Nakamura, Eiichi,Kubota, Katsumi,Isaka, Masahiko
, p. 5809 - 5810 (2007/10/02)
Stereoselective vinylcupration of a cyclopropenone acetal (1), followed by in situ electrophilic trapping with an alkylating agent, affords via a cis-substituted vinylcyclopropane 2, which stereoselectively rearranges to the acetal of a cross-conjugate di
