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.
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.
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Terai,Tanaka
, p. 822 (1956)
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Okano,M.
, p. 1041 - 1046 (1976)
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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.
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.
