- FREE RADICAL ADDITION OF α-BROMOCARBOXYLIC ACIDS TO OLEFINS LEADING TO γ-BUTYROLACTONES
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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.
- Nakano, Taichi,Kayama, Mikio,Matsumoto, Hideyuki,Nagai, Yoichiro
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- Synthesis of deuterated γ-lactones for use in stable isotope dilution assays
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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.
- Hislop, J.O.-Anna,Hunt, Martin B.,Fielder, Simon,Rowan, Daryl D.
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- W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid
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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.
- Xie, Zhong-Yu,Deng, Jin,Fu, Yao
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- Intermolecular additions of α-boryl radicals
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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.
- Batey, Robert A.,Pedram, Bijan,Yong, Kelvin,Baquer, Gemma
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- Free Radical Addition of 2-Bromoalkanoic Acids to Alkenes
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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.
- Nakano, Taichi,Kayama, Mikio,Nagai, Yoichiro
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- A general synthesis of (+)-γ-substituted γ-butyrolactones using a kinetic alkylation-ozonolysis procedure
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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.
- Gavin,Geraghty
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- A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles
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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.
- Pollock, Julie A.,Clark, Karen M.,Martynowicz, Bethany J.,Pridgeon, Matthew G.,Rycenga, Matthew J.,Stolle, Kristen E.,Taylor, Stephen K.
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- Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol
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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.
- Qi, Chenxiao,Yang, Shengwen,Gandon, Vincent,Leb?uf, David
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supporting information
p. 7405 - 7409
(2019/10/02)
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- Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool to Study Photoredox Reactions
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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.
- Triandafillidi, Ierasia,Kokotou, Maroula G.,Kokotos, Christoforos G.
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supporting information
p. 36 - 39
(2018/01/17)
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- Electroreductive coupling of aromatic ketones, aldehydes, and aldimines with α,β-unsaturated esters: Synthesis of 5-aryl substituted γ-butyrolactones and lactams
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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.
- Kise, Naoki,Hamada, Yusuke,Sakurai, Toshihiko
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p. 1143 - 1156
(2017/02/18)
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- Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
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An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
- Richers, Johannes,Heilmann, Michael,Drees, Markus,Tiefenbacher, Konrad
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p. 6472 - 6475
(2016/12/23)
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- 1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents
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The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents
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The present invention primarily relates to imidazo[1,2-a]pyridine-ylmethyl-derivatives of Formula (I) wherein R1, R2, X, W e J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.
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- Ruthenium pincer-catalyzed synthesis of substituted γ-butyrolactones using hydrogen autotransfer methodology
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The ruthenium pincer-catalyzed synthesis of γ-butyrolactones from 1,2-diols and malonates using borrowing-hydrogen methodology is reported. This regioselective domino-process takes place through catalytic C-C bond formation, followed by intramolecular transesterification. Herein, we show the Ru-MACHO-BH complex as a valuable catalyst in hydrogen autotransfer reactions.
- Pe?a-López, Miguel,Neumann, Helfried,Beller, Matthias
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supporting information
p. 13082 - 13085
(2015/08/18)
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- INFANT FORMULA CONTAINING AN AROMA COMPOSITION FOR USE AS FRAGRANCE
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The invention relates to a nutraceutical composition such as infant formula or infant food comprising a) a defined aroma composition; b) a methodology for developing, maintaining certain aroma constituents in the infant formula and an aroma or fragrance composition to be used to increase the acceptance of a person or an object by the baby or new born.
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- Enantioselective synthesis of syn / anti -1,3-amino alcohols via proline-catalyzed sequential α-aminoxylation/α-amination and horner-wadsworth-emmons olefination of aldehydes
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(Figure presented) A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential α-aminoxylation/ α-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5- phenylpentan-2-ol, is also accomplished.
- Jha, Vishwajeet,Kondekar, Nagendra B.,Kumar, Pradeep
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supporting information; experimental part
p. 2762 - 2765
(2010/08/19)
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- Unusual transformation of (1R,1′S,2S)-1-(3-diisopropylamino-3- oxopropyl)-2-(1-hydroxyethyl)cyclopropane in the course of the cyclopropylcarbinyl rearrangement
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The cyclopropylcarbinyl rearrangement of (1R,1′ S,2S)-1-(3- diisopropylamino-3-oxo-propyl)-2-(1-hydroxyethyl)cyclopropane and the participation of the amide moiety in the intramolecular process smoothly affords the (2′ E,5S)- N,N-diisopropyl-N-[5-(but-2′-
- Zlokazov,Veselovsky
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experimental part
p. 322 - 326
(2010/07/09)
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- Iterative approach to enantiopure synlanti-1,3-polyols via proline-catalyzed sequential a-aminoxylation and horner-wadsworth-emmons olefination of aldehvdes
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Iterative use of proline-catalyzed tandem α-aminoxylation and HWE olefination of aldehydes provided a simple access to 1,3-polyols. The feasibility of this approach is initially studied to synthesize syn- and anti-1,3-diols and is further extended to a syn/syn-1,3,5-triol at a useful level of asymmetric induction and yield. Its usage is illustrated by the short synthesis of a hydroxylactone pheromone component, (2S,3S)-2- hydroxyhexylcyclopentanone.
- Kondekar, Nagendra B.,Kumar, Pradeep
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body text
p. 2611 - 2614
(2009/10/23)
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- Oxidative addition of chloro- and dichloroacetic acid to alkenes to give α-chloro- and α,α-dichlorobutyrolactones with manganese(III) acetate
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Oxidative addition of chloroacetic acid and dichloroacetic acid to alkenes with Mn(OAc)3 to give α-chloro- and α,α -dichlorobutyrolactones proceeds in moderate to good yield in MeCN containing one equivalent of the sodium salt of the carboxylic
- Snider, Barry B.,Che, Qinglin
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p. 325 - 332
(2007/10/03)
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Precursor compounds
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The compounds of the formula I are precursors for organoleptic and antimicrobial compounds. The latter are generated in the presence of skin bacteria, enzymes or acidic or alkaline conditions. One precursor molecule can provide one or more different compounds.
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- Beta-ketoester compounds
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The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.
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- Synthesis and absolute stereochemistry of Hagen's-Gland lactones in some parasitic wasps (Hymenoptera:Braconidae)
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Efficient syntheses and enantioselective gas chromatography have confirmed the structures and established the absolute stcreochemistry of some novel bicyclic lactones (tetrahydrofurofuranones) in species of parasitic wasps (Hymenoptera:Braconidae). The co-occurring γ-lactones, octan-4-olide and dodecan-4-olide, have the (R)-configuation.
- Paddon-Jones, Gregory C.,Moore, Christopher J.,Brecknell, Douglas J.,Koenig, Wilfried A.,Kitching, William
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p. 3479 - 3482
(2007/10/03)
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- Decane autoxidation: Precursors of gamma lactones and other minor products
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Autoxidation of decane produces the following minor products in decreasing yields, viz. 2,5-, 3,6- and 4,7-decanediones and diols. Addition of 3-decanone to a decane autoxidation enhances the production of octanal, heptanal, octanoic and heptanoic acids. 3-Decanol initially inhibits the autoxidation reaction prior to being oxidized to 3-decanone. γ-Octanoic and γ-heptanoic lactone formation in the autoxidation of decane is promoted by the addition of 3- and 4-decyl hydroperoxides, respectively. These lactones are formed when tert-butoxy radicals react with 3,6- and 4,7-decane diols in the presence of oxygen. The nature of the intermediates in the formation of the minor products and the inhibition by alcohols are discussed.
- Goosen, Andre,Kindermans, Sybrandus
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- Oxidation of Diols with Sodium Bromite Trihydrate in Organic Solvents in the Presence of Alumina
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The title oxidation of diols with two primary hydroxy groups (symmetrical diols) and those with both a primary and a secondary hydroxy group (unsymmetrical diols) gives the corresponding lactones or the hydroxy ketones, being dependent upon the types of diols.
- Morimoto, Takashi,Hirano, Masao,Iwasaki, Keiko,Ishikawa, Takashi
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- Reactions of hydriodic acid with aldonolactones and n-alkanolactones. Interconversions between lactones and iodocarboxylic acids
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Aldonolactones containing from four to eight carbon atoms, and lactones of the related monohydroxy-n-alkanoic acids, were subjected to reaction with 57 percent hydriodic acid at 125 deg C.As in the classical studies of Kiliani, the reduction of D-glycero-D-ido-heptono-1,4-lactone yielded mainly γ-heptanolactone.Analogously, the corresponding γ-alkanolactones were obtained as major products from the 1,4-lactones of the D-xylono, D-allono-, and D-erythro-L-talo-octono configuration.Monoiodo-n-alkanoic acids were also formed in admixture with the lactones in all of these reactions.D-Erythrono-1,4-lactone was unique among the aldonolactones in that it led only to an acid, i.e., 3-iodo-n-butanoic acid.The latter was also the product of the non-reductive reaction of hydriodic acid with β-butyrolactone whereas, by contrast, γ-butyrolactone afforded 4-iodobutanoic acid.Among compounds in the five to eight carbon series, it was found that under conditions close to equilibrium the ratio of lactone to iodoacid decreased progressively with the length of the carbon chain; e.g., in the 4 h reactions of γ-valero, γ-capro, γ-heptano,- and γ-octanolactone, the ratios were 2.4, 1.2, 0.2, and 0.1, respectively.An accompanying characteristic of these reactions is a progression in the number of isomeric iodoacids formed.Whereas γ-valerolactone was accompanied by 4-iodopentanoic acid, there were two isomers (4- and 5-) of iodohexanoic acid, three monoiodo- (including 6-iodo-) heptanoic acids, and four (including 7-iodo-) octanoic acids.In all instances, the isomer substituted at the penultimate carbon was major.An interplay of several individual reactions, including ring-opening displacements, eliminations-additions, and rearrangements, as well as a probable influence of entropy changes on the lactone-acid equilibria, appear to account largely for these observations.
- Liu, Zhengchun,Granata, Alessandro,Shen, Xinhua,Perlin, Arthur S.
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p. 2081 - 2088
(2007/10/02)
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- A NEW ROUTE TO γ-SUBSTITUTED γ-LACTONES AND δ-SUBSTITUTED δ-LACTONES BASED ON THE REGIOSELECTIVE β-SCISSION OF ALKOXY RADICALS GENERATED FROM TRANSANNULAR HEMIACETALS
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A new general synthesis of γ-substituted γ-lactones and δ-substituted δ-lactones including dihydro-5-octyl-2(3H)-furanone, a natural pheromone, is described.The synthesis involves the regioselective β-scission of alkoxy radicals generated from transannular hemiacetals as the key step. Key Words: γ-Lactones; δ-Lactones; Mercury(II) Oxide-Iodine Reagent; Photolysis; β-Scission of Alkoxyl Radicals
- Kobayashi, Kazuhiro,Sasaki, Akiyoshi,Kanno, Yoshikazu,Suginome, Hiroshi
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p. 7245 - 7258
(2007/10/02)
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- N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide as Thiohomoenolatesynthon. Application to a Synthesis of Some Heterocycles
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N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide undergoes metalexchange with n-butyllithium.The resulting thiohomoenolate dianion reacts with elestrophiles (aldehydes and ketones) to give the γ-hydroxythioamides, which are transformed into lactones, iminothiolactones, and thiolactams with simple elaboration.
- Takahata, Hiroki,Ohkura, Etsuko,Ikuro, Kazumi,Yamazaki, Takao
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p. 285 - 292
(2007/10/02)
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- N-IODOSUCCINIMIDE MEDIATED OXIDATIVE CYCLIZATION OF MONO-t-BUTYLDIMETHYLSILYLATED DIOLS
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The oxidation of mono-t-butyldimethylsilylated diols is described.The t-butyldimethylsilyl moiety is useful for controlling both the direction of cyclization and the size of ring being formed.
- McDonald, Chriss E.,Beebe, Thomas R.,Beard, Mark,McMillen, Doug,Selski, Daniel
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p. 4791 - 4794
(2007/10/02)
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- SOLVOLYTIC HYDROPEROXIDE REARRANGEMENTS IV. Selective Rearrangement of Spirooctan-4-ol.
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Rearrangement of spirooctan-4-ol, 1, in acidified THF-H2O2 is a selective process in which substitution occurs with retention of configuration and ring-expansion with inversion of the carbinyl center.
- Ronald, Robert C.,Ruder, Suzanne M.,Lillie, Thomas S.
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p. 131 - 134
(2007/10/02)
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- MECHANISM OF THE ADDITION OF TRIBUTYLTIN IODOACETATE TO ALKENES
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The mechanism of the formation of lactones by free radical additions of tri-n-butyltin iodoacetate to alkenes occurs through a two-step process: a homolytic addition of the ester (addition of .CH2-CO2SnBu3, iodine transfer), followed by a fast ionic cyclization with elimination of tri-n-butyltin iodide.
- Degueil-Castaing, M.,Jeso, B. De,Kraus, G. A.,Landgrebe, K.,Maillard, B.
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p. 5927 - 5930
(2007/10/02)
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- STANNYL ESTER CYCLIZATIONS
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Alpha halo stannyl esters react with alkenes to afford lactones.The reaction is catalyzed by AIBN.The reaction proceeds best with electron rich alkenes.The mechanistic aspects of this novel reaction are discussed.This reaction can also be conducted intramolecularly to produce bicyclic lactones.An approach to the lignan system is presented.
- Kraus, George A.,Landgrebe, Kevin
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p. 4039 - 4046
(2007/10/02)
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- γ-BUTYROLACTONE AUS METALLIERTEN ENAMINEN
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Enamines of type 1 with anion-stabilizing substituents a are available by Horner-reaction of suitable phosphonates aldehydes.Deprotonation of 1 gives aminoallyl anions 2, which react with carbonyl compounds (depending on a) either to butyrolactones 8 resp. 10 or to 6-membered lactons 13.This process amounts to synthesis of lactones from two carbonyl compounds and an α-aminosubstituted phosphonate.
- Costisella, Burkard,Gross, Hans,Schick, Hans
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p. 733 - 736
(2007/10/02)
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- THE TRANSFORMATION OF ALKENES INTO γ-LACTONES USING α-IODOESTERS
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Iodostannyl esters react with alkenes in the presence of AIBN to afford γ-lactones.
- Kraus, George A.,Landgrebe, Kevin
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p. 3939 - 3942
(2007/10/02)
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- Synthesis of γ- and δ-Lactones via Radical CC-Bond Formation Reaction
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Lactones 5 and 6 can be synthesized via solvomercuration of alkenes 1 and reductive CC-bond formation with acrylonitrile.
- Giese, Bernd,Hasskerl, Thomas,Luening, Ulrich
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p. 859 - 861
(2007/10/02)
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- Direct Oxidation of Alkanoic Acids and their Amides to γ-Lactones by Peroxydisulphate-containing Systems
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The reaction of one-electron oxidation of alkanoic acids (I) and their amides (VI) on treatment with Na2S2O8-containing systems has been studied.As a result of the direct one-pot reaction acids (I) and amides (VI) are converted into γ and δ-lactones, the reaction being regioselective and leading mainly to γ-lactones in up to 35percent yield.The regioselectivity of the oxidative lactonisation depends greatly on the nature of alkyl substituents.The results obtained are presented in terms of a mechanism suggesting the generation of acyloxyl and amidyl radicals from (I) and (VI), respectively, followed by a rearrangement via a 1,5- or 1,6-H shift into the corresponding 3- and 4-carboxy- or -carboxamido-alkyl ra The latter undergo oxidative cyclisation to produce γ and δ lactones.The system Na2S2O8-NaCl-NaOH converts carboxamides (VI) into amines with loss of one carbon atom as a result of a Hoffmann type rearrangement.
- Nikishin, Gennady I.,Svitanko, Igor V.,Troyansky, Emmanuil I.
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p. 595 - 602
(2007/10/02)
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- TRIPHENYLCARBENIUM AND TRIS(P-BROMOPHENYL)AMMONIUMYL ION INDUCED LACTONIZATIONS OF ω-BENZYLOXY AND ω-P-METHOXYBENZYLOXY METHYL ESTERS
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The title reaction leads to smooth generation of five and six membered lactones via direct nucleophilic participation of the carbomethoxy group in intermediates of type 3.
- Hoye, Thomas R.,Kurth, Mark J.,Lo, Vincent
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p. 815 - 818
(2007/10/02)
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