1679-36-3Relevant articles and documents
Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition
Zhang, Yanshun,Sun, Yaoliang,Wei, Yin,Shi, Min
supporting information, p. 2129 - 2135 (2019/03/13)
A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).
Catalytic enantioselective construction of β-quaternary carbons via a conjugate addition of cyanide to β,β-disubstituted α,β-unsaturated carbonyl compounds
Tanaka, Yuta,Kanai, Motomu,Shibasaki, Masakatsu
supporting information; experimental part, p. 8862 - 8863 (2010/08/21)
The first general catalytic enantioselective conjugate addition of cyanide to β, β-disubstituted α,β-unsaturated ketones and N-acylpyrroles was developed using a strontium catalyst derived from Sr(O iPr)2 and new chiral ligand 5. The reaction exhibited excellent enantioselectivity and a wide substrate scope using 0.5-10 mol % catalyst. 1,4-Adducts containing β-quaternary carbons were exclusively produced over 1,2-adducts. ESI-MS analysis of the strontium catalyst indicated that the active catalyst was a trimetallic Sr/5 = 3:5 complex. The exclusive 1,4-selectivity was partly due to the ability of the strontium complex to promote both a retro-cyanation reaction from the 1,2-adducts and highly enantioselective conjugate cyanation.
Chromium catalyzed oxidation of (homo-)allylic and (homo-)propargylic alcohols with sodium periodate to ketones or carboxylic acids
De Vondervoort, Lizette Schmieder-Van,Bouttemy, Sabine,Padrón, José M.,Le Bras, Jean,Muzart, Jacques,Alsters, Paul L.
, p. 243 - 246 (2007/10/03)
Primary and secondary (homo-)allylic and (homo-)propargylic alcohols can be oxidized under slightly acidic conditions at or below room- temperature with sodium periodate in the presence of sodium dichromate as the catalyst to the corresponding carboxylic acids and ketones, respectively.
PalladiumdD-catalyzed exchange and isomerization reactions. 17. Exchange of chiral allyl alcohols with hydroxide, methoxide, and phenyl at high [Cl-]. Stereochemistry of the wacker reaction
Hamed, Othman,Henry, Patrick M.,Thompson, Charles
, p. 7745 - 7750 (2007/10/03)
At high [Cl ] (> 2.0 M), PdCl42- catalyzes the exchange of chiral allylic alcohols with hydroxy, methoxy, and phenyl to give chiral allyl-substituted olefins. With unsymmetrical olefins, isomerization occurs along with exchange. The hydroxyl exchange occurs in aqueous solution while the other exchanges are carried out in methanol solution. At low [Cl-] (0.1 M) oxidation to the corresponding β-hydroxy-, methoxy-, and phenyl-substituted carbonyl compounds occurred. The absolute configurations of the oxidation and exchange products should be the same if the same mode of addition to the Pd(II)-β-complex is operative. The absolute configurations of the oxidation and exchange products for the phenylation reaction were the same, while for hydroxy and methoxy they were different. This result indicates methanol and water must have different stereochemistries of addition at high and low [Cl-]. Thus, previous studies showing anti hydroxypalladation at high [Cl-] are not valid indicators of the stereochemistry at low [Cl-]. If anti addition occurs at high [Cl-], the addition must be syn at low [Cl-].
Oxygenation of alkynes to α,β-acetylenic ketones with dioxygen catalyzed by N-hydroxyphthalimide combined with a transition metal
Sakaguchi, Satoshi,Takase, Tomoyuki,Iwahama, Takahiro,Ishii, Yasutaka
, p. 2037 - 2038 (2007/10/03)
Alkynes were successfully converted into α,β-acetylenic carbonyl compounds through radical-catalyzed aerobic oxidation using N-hydroxyphthalimide (NHPI) combined with a transion metal under mild conditions.
Concerning the formations of α-iodoenones
Bovonsombat, Pakorn,Angara, Geetha J.,Mc Nelis, Edward
, p. 6787 - 6790 (2007/10/02)
The formations of α-iodoenones from secondary alkynols with NIS/HTIB (cat.), tertiary alkynols with I2/PDC and enones with I2/pyridine have been compared. In the latter two reactions the PDC and the pyridine have been found to be catalytic.
REACTION OF HYDROXY AND CARBONYL COMPOUNDS WITH SULFUR TETRAFLUORIDE. IX. REACTIONS OF ALIPHATIC β-DIKETONES WITH SF4
Stepanov, I. V.,Burmakov, A. I.,Kunshenko, B. V.,Alekseeva, L. A.,Yagupol'skii, L. M.
, p. 244 - 248 (2007/10/02)
Aliphatic β-diketones react with sulfur tetrafluoride to form the corresponding di- and tetrafluoro derivatives and also compounds containing double and triple carbon-carbon bonds.In the reactions of 1,1,1-trifluoro derivatives of β-diketones with sulfur tetrafluoride the acyl fluoride is eliminated, and 1,1,1,2-tetrafluoropropene is obtained.Hexafluoroacetylacetone only forms 3-hydroperfluoro-2-pentene under the influence of sulfur tetrafluoride.
