104-50-7Relevant articles and documents
FREE RADICAL ADDITION OF α-BROMOCARBOXYLIC ACIDS TO OLEFINS LEADING TO γ-BUTYROLACTONES
Nakano, Taichi,Kayama, Mikio,Matsumoto, Hideyuki,Nagai, Yoichiro
, p. 415 - 418 (1981)
Benzoyl peroxide-catalyzed free radical addition of bromoacetic, α-bromopropionic, and α-bromobutyric acids to olefins took place under mild conditions to afford γ-alkyl-, γ-alkyl-α-methyl-, and γ-alkyl-α-ethyl-γ-butyrolactones in good yields.
Synthesis of deuterated γ-lactones for use in stable isotope dilution assays
Hislop, J.O.-Anna,Hunt, Martin B.,Fielder, Simon,Rowan, Daryl D.
, p. 7075 - 7083 (2004)
Two syntheses of deuterated γ-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3- 2H4]-γ-Octa-, -γ-deca-, and -γ-dodecalactones with >89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-2H 3]-γ-Octa- and -γ-dodecalactones were prepared in 6 and 23% yields with >92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-2H3]-1-hexene and [1,1,2- 2H3]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated γ-lactones were evaluated as internal standards for SIDA.
W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid
Xie, Zhong-Yu,Deng, Jin,Fu, Yao
, p. 2332 - 2339 (2018)
γ-Lactones are an important class of fine chemical products and are widely used in perfumes, medicines, pesticides, dyes, and other fields. Herein, a new method for γ-lactones preparation based on ring contraction was developed. Starting from macrolides, W(OTf)6 was used to catalyze the ring-opening polymerization then depolymerization. The depolymerization step was not a common ring-closing process, and the carbon number of the ring was reduced one by one by rearrangement to form the most thermodynamically stable five-membered ring compounds. γ-Caprolactone (180 °C for 10 h) was obtained in a yield of 94 % when [EMIM]OTf was used as the solvent, and the yield of isolated product was up to 85 %. The interaction of various components and the reaction mechanism were studied by FTIR spectroscopy and 1H NMR spectroscopy, respectively. Furthermore, γ-lactones could be produced when the substrate was extended to terminal hydroxyfatty acids. Unexpectedly, the catalyst was poisoned by 1 equivalent of H2O added during the process and thus the yield decreased greatly. The reaction is green and simple, and proceeds in one pot with high atom economy (100 % for macrolides and with water as the only byproduct for terminal hydroxyfatty acid), which provides a promising approach to synthesizing γ-lactones.
Intermolecular additions of α-boryl radicals
Batey, Robert A.,Pedram, Bijan,Yong, Kelvin,Baquer, Gemma
, p. 6847 - 6850 (1996)
The utility of α-boryl radicals 1 in intermolecular addition processes is described. Boronic ester substituted radicals are shown to add to both electron deficient and electron rich radical traps, and give high yields of homoallylboronic esters in radical allylation reactions.
Free Radical Addition of 2-Bromoalkanoic Acids to Alkenes
Nakano, Taichi,Kayama, Mikio,Nagai, Yoichiro
, p. 1049 - 1052 (1987)
The benzoyl peroxide-catalyzed reaction of 2-bromoalkanoic acids such as bromoacetic, 2-bromopropionic, and 2-bromobutyric acid with 1-alkenes was found to proceed thorough the addition of the C-Br bond across the double bond followed by cyclization affording 4-alkanolides in good yields.
A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure
Gavin,Geraghty
, p. 1351 - 1361 (1994)
A synthesis of (±)-γ-substituted γ-butyrolactones is described in which the key intermediates, γ-ketoesters, are prepared from the readily available 6-methyl-5-hepten-2-one using a kinetic alkylation-ozonolysis procedure; the method allows terminal ester and Z-alkene groups to be incorporated into the side-chain and thus can be used for the synthesis of (+)-γ-jasmolactone as well as other naturally occurring lactones.
A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles
Pollock, Julie A.,Clark, Karen M.,Martynowicz, Bethany J.,Pridgeon, Matthew G.,Rycenga, Matthew J.,Stolle, Kristen E.,Taylor, Stephen K.
, p. 1888 - 1892 (2007)
We have developed a biocatalytic method to produce lactones and related compounds via the enzymatic hydrolysis of γ- and β-hydroxynitriles. The synthesis is a mild, general, and environmentally friendly way to enantioselectively hydrolyze nitriles with commercially available nitrilase enzymes. The synthesis of four pheromones is demonstrated via a one-step method.
Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
Qi, Chenxiao,Yang, Shengwen,Gandon, Vincent,Leb?uf, David
supporting information, p. 7405 - 7409 (2019/10/02)
We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.
Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions
Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.
supporting information, p. 36 - 39 (2018/01/17)
A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)3Cl2 as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry.
Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko
, p. 1143 - 1156 (2017/02/18)
The electroreductive intermolecular coupling of aromatic ketones and aldehydes with α,β-unsaturated esters in the presence of TMSCl gave the adducts as γ-trimethylsiloxy esters. The detrimethylsilylation of the adducts with TBAF afforded 5-aryl substituted γ-butyrolactones. The electroreductive coupling of N-(4-methoxyphenyl)-1-arylmethaneimines with methyl acrylate in the presence of TMSCl gave the adducts as methyl 4-aryl-4-((4-methoxyphenyl)amino)butanoates. The adducts were transformed to 5-aryl-γ-butyrolactams by cyclization with NaH and subsequent oxidation with CAN. (±)-Norcotinine was prepared from nicotinaldehyde by this method. The electroreductive coupling of aromatic ketones and aldimines with acrylonitrile in the presence of TMSCl gave 4-aryl-4-(trimethylsiloxy)butanenitriles and 4-aryl-4-((4-methoxyphenyl)amino)butanenitriles, respectively.
