10606-64-1Relevant academic research and scientific papers
Regioselective Synthesis of γ-Lactones by Iron-Catalyzed Radical Annulation of Alkenes with α-Halocarboxylic Acids and Their Derivatives
Iwasaki, Masayuki,Miki, Natsumi,Ikemoto, Yuichi,Ura, Yasuyuki,Nishihara, Yasushi
, p. 3848 - 3852 (2018)
An abundant and low toxicity iron catalyst has enabled regioselective annulation of alkenes with α-halocarboxylic acids and their derivatives. The reaction proceeds smoothly without any additional ligands, bases, and additives to afford a variety of γ-lactones in good yields. A proposed reaction pathway through radical annulation is supported by some mechanistic studies, involving radical clock and isotope labeling experiments. The present method was applied to the practical iron-powder-promoted synthesis of γ-lactones.
Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes
Kataoka, Yasutaka,Komori, Saki,Shimizu, Yuhei,Tanaka, Rina,Ura, Yasuyuki
, p. 570 - 574 (2022/02/02)
1,1-Disubstituted alkenes feature high steric hindrance, which renders their Wacker-type oxidation difficult. We demonstrate the stereoselective synthesis of 2-hydroxytetrahydrofurans via the Wacker-type oxidation of 3-methyl-3-buten-1-ols by using a PdCl
Pd(ii)/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids
Zhang, Xuexin,Gao, Yang,Laishram, Ronibala Devi,Li, Kangkui,Yang, Yong,Zhan, Yong,Luo, Yang,Fan, Baomin
supporting information, p. 2174 - 2181 (2019/02/27)
An efficient Pd/Zn co-catalyzed chemo-selective hydrogenation of α-methylene-γ-keto carboxylic acids is described. This methodology offers a divergent synthesis of α-methyl-γ-keto carboxylic acids, α-methylcarboxylic acids, and lactones starting from α-me
Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids
Duhamel, Thomas,Mu?iz, Kilian
supporting information, p. 933 - 936 (2019/01/23)
A new method for the formation of γ- and δ-lactones from carboxylic acids through direct conversion of benzylic C-H to C-O bonds is described. The reaction is conveniently induced by visible light and relies on a mild cooperative catalysis by the combination of molecular iodine and an organic dye.
MnO2-promoted carboesterification of alkenes with anhydrides: A facile approach to γ-lactones
Wu, Lihuan,Zhang, Zhenming,Liao, Jianhua,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 2628 - 2631 (2016/02/18)
An efficient carboesterification of alkenes with anhydrides promoted by MnO2 has been developed to afford functionalized γ-lactones in good to excellent yields. This method shows a broad substrate scope and provides a valuable and convenient synthetic tool for constructing γ-lactones.
Copper-catalyzed intermolecular oxidative [3 + 2] cycloaddition between alkenes and anhydrides: A new synthetic approach to γ-lactones
Huang, Liangbin,Jiang, Huanfeng,Qi, Chaorong,Liu, Xiaohang
supporting information; experimental part, p. 17652 - 17654 (2011/03/16)
A new copper-catalyzed oxidative [3 + 2] cycloaddition of alkenes with anhydrides using oxygen as the sole oxidant to afford γ-lactones has been developed. This catalyzed cyclization process has a broad substrate scope and affords γ-lactones in good to excellent yields.
Intramolecular nucleophilic acyl substitution reactions mediated by XTi(O-i-Pr)3 (X = Cl, O-i-Pr)/2i-PrMgBr reagent. Efficient synthesis of functionalized organotitanium compounds from unsaturated compounds
Okamoto,Kasatkin,Zubaidha,Sato
, p. 2208 - 2216 (2007/10/03)
Treatment of acetylenic or olefinic carbonates and esters with a low-valent titanium reagent diisopropoxy(η2-propene)titanium (1), readily generated by the reaction of Ti(O-i-Pr)4 or ClTi(O-i-Pr)3 with 2i-PtMgX, resulted in an intramolecular nucleophilic acyl substitution (INAS) reaction to afford organotitanium compounds having a carbonyl functional group, in good to excellent yields. Thus, the treatment of alkyl alkynyl carbonates 2 or alkyl alkenyl carbonates 4 with 1 gave organotitanium compounds having a lactone and/or ester group. Similarly, alkyl alkynoates 10 or alkynyl esters 14 of carboxylic acids reacted with 1 to give organotitanium compounds having a cyclic or acyclic ketone group, respectively. Thus, the reaction provides, after hydrolysis, five- or six-membered α-alkylidene lactones and/or α,β-unsaturated esters from 2, γ-butyrolactone derivatives from 4, five- or six-membered α-alkylidene cyclic ketones from 10, and acyclic α,β-unsaturated ketones 15 from 14. In all cases, the yields are excellent and the generation of the organotitanium compounds was confirmed by deuterolysis. The organotitaniums 6 and 11c reacted smoothly with iodine to afford 2-(iodomethyl)-4-butanolide (9) and α-[iodo(trimethylsilyl)methylidene]cyclopentanone, respectively. The organotitanium compounds obtained here also reacted with aldehydes to give the corresponding adducts, thus opening up a new access to substituted α,β-butenolides from 2, to γ-butyrolactones from 4, and to the corresponding tetrasubstituted furan from 10 and 14.
Samarium(II) Di-iodide Induced Reductive Coupling of α,β-Unsaturated Esters with Carbonyl Compounds Leading to a Facile Synthesis of γ-Lactone
Fukuzawa, Shin-ichi,Nakanishi, Akira,Fujinami, Tatsuo,Sakai, Shizuyoshi
, p. 1669 - 1676 (2007/10/02)
Samarium(II) di-iodide, which is a strong one-electron transfer reducing agent, is effective for the reductive coupling of α,β-unsaturated esters with carbonyl compounds, whereby substituted γ-lactones can easily be prepared in good to excellent yields under very mild conditions.Two mole equiv. of samarium(II) di-iodide to each mole equiv. of starting substrate always give reasonable yields.The presence of an alcohol is essential in the reaction, complex unidentified products being formed in the absence of an alcohol; t-butyl alcohol gave more satisfactory results than methanol and ethanol.The alcohol acts as a proton donor, the use of MeOD leading to a deuteriated γ-lactone.The reaction is applicable to both aliphatic and aromatic ketones or aldehydes, whereas the electrochemical method is limited to aliphatic substrates.The diastereoselectivity is examined in the reaction of 4-t-butylcyclo-hexanone with ethyl acrylate; an anti-isomer is produced predominantly (syn:anti = 1:9) as the result of selective axial attack.The reaction may proceed by a radical mechanism, and reaction may not involve a samarium ester homoenolate.The reaction is extended to the intramolecular reaction of an α,β-unsaturated keto ester (8-oxonon-2-enoate) leading to the ready synthesis of a bicyclic γ-lactone.
