38836-24-7Relevant academic research and scientific papers
MnO2as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins
Fernandes, Rodney A.,Ramakrishna, Gujjula V.,Bethi, Venkati
, p. 6115 - 6125 (2020/10/27)
Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
A useful synthetic equivalent of an acetone enolate
Maslak, Veselin,Tokic-Vujosevic, Zorana,Ferjancic, Zorana,Saicic, Radomir N.
experimental part, p. 6709 - 6711 (2010/01/18)
2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed wit
A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α,β-unsaturated ketones
Kourouli, Therapia,Kefalas, Panagiotis,Ragoussis, Nikitas,Ragoussis, Valentine
, p. 4615 - 4618 (2007/10/03)
A general and convenient synthesis of β-ketols and α,β-alkenones has been achieved by a Knoevenagel condensation of a β-ketoacid with an aldehyde in aqueous medium. Saponification of a β-ketoester by an aqueous KOH 10% solution gives the potassium salt of the β-ketoacid, which is condensed in situ with an aldehyde at pH 7.8-8.0, at 60 °C for 5-6 h. The intermediate β-ketocarboxylate is smoothly decarboxylated in the reaction medium, giving the β-ketol in high yield (75-90%). Acidification of the reaction mixture at pH 1 and heating at 70 °C under vigorous stirring for 6 h, leads directly to the corresponding α,β-unsaturated ketone in good yield (65-75%).
A highly chemoselective Mukaiyama aldol reaction of saturated aldehyde over unsaturated aldehyde with enol tris(2,6-diphenylbenzyl)silyl ether
Shirakawa, Seiji,Maruoka, Keiji
, p. 1469 - 1472 (2007/10/03)
An exceedingly high chemoselective Mukaiyama aldol reaction of saturated aldehydes in the presence of unsaturated aldehydes (benzaldehyde and α,β-enals) has been realized for the first time by using the structurally unique enol tris(2,6-diphenylbenzyl)sil
Acetonyltriphenylphosphonium bromide and its polymer-supported analogues as catalysts in protection and deprotection of alcohols as alkyl vinyl ethers
Hon, Yung-Son,Lee, Chia-Fu,Chen, Rong-Jiunn,Szu, Ping-Hui
, p. 5991 - 6001 (2007/10/03)
Both acetonyltriphenylphosphonium bromide (ATPB, 1) and poly-p-styryldiphenylacetonylphosphonium bromide (A) were effective catalysts in the protection of alcohols as THP, THF, and EE ethers as well as the cleavage of THP, THF, and EE ethers to the corresponding alcohols. They could be applied to 1°, 2° and 3° alcohols, phenol and acid-labile alcohols. Both ATPB and catalyst A are excellent catalysts in the present study. It needed only 1×10-2-1.25×10-2 mol equiv. of the polymer-supported catalyst A in the reactions.
Electroreductive Ring-Opening of α,β-Epoxy Carbonyl Compounds and Their Homologues through Recyclable Use of Diphenyl Diselenide or Diphenyl Ditelluride as a Mediator
Inokuchi, Tsutomu,Kusumoto, Masahiko,Torii, Sigeru
, p. 1548 - 1553 (2007/10/02)
A novel access to β-hydroxy carbonyl compounds from the corresponding α,β-epoxy compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electroreduction mediator in a MeOH-NaClO4-(Pt) system. α,β-Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters.Similarly, α,β-epoxy esters and nitriles can be reduced to the corresponding β-hydroxy compounds in the presence of acetic acid.
OXIDATION OF ISOXAZOLINES BY PERACIDS - A USEFUL ROUTE TO β-HYDROXY KETONES AND ACYLATED DIOLS
Park, Pyeong-uk,Kozikowski, Alan P.
, p. 6703 - 6706 (2007/10/02)
A method for bringing about the ring cleavage of isoxazolines by the use of peracids is described.
A NEW SYNTHETIC METHOD FOR γ-BUTYROLACTOLS BY THE PALLADIUM-CATALYZED REGIOSELECTIVE OXIDATION OF 1-ALKEN-4-OLS
Nokami, Junzo,Ogawa, Hideki,Miyamoto, Shinya,Mandai, Tadakatsu,Wakabayahi, Shoji,Tsuji, Jiro
, p. 5181 - 5184 (2007/10/02)
3-substituted 1-alken-4-ols were oxidized with PdCl2-benzoquinone regioselectively at the terminal carbon to afford cyclic hemiacetals (γ-butyroacetols), which were converted to γ-butiroacetones by the Jones oxidation.This reactions was applied to the synthesis of optically active deoxyribose and γ-butenolides.
Methods for the Conversion of Isoxazolines to β-Hydroxy Ketones
Kozikowski, Alan P.,Adamczyk, Maciej
, p. 3123 - 3126 (2007/10/02)
Two methods have been developed for converting isoxazolines to β-hydroxy ketones in a stereospecific manner.
