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Cas Database

1008-73-7

1008-73-7

Identification

  • Product Name:2(3H)-Furanone,dihydro-4-phenyl-

  • CAS Number: 1008-73-7

  • EINECS:

  • Molecular Weight:162.188

  • Molecular Formula: C10H10 O2

  • HS Code:2932209090

  • Mol File:1008-73-7.mol

Synonyms:Hydrocinnamicacid, b-(hydroxymethyl)-, g-lactone (7CI);4-Phenyldihydrofuran-2(3H)-one; 4-Phenyldihydrofuran-2-one; Benzenepropanoicacid, b-(hydroxymethyl)-, g-lactone;Dihydro-4-phenyl-2(3H)-furanone; NSC 1108; b-Phenyl-g-butyrolactone; b-Phenylbutyrolactone

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:4-Phenyloxolan-2-one
  • Packaging:100mg
  • Price:$ 260
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:4-Phenyloxolan-2-one
  • Packaging:10mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:DIHYDRO-4-PHENYLFURAN-2(3H)-ONE 95.00%
  • Packaging:5MG
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Relevant articles and documentsAll total 121 Articles be found

An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation

Imada, Yasushi,Iida, Hiroki,Murahashi, Shun-Ichi,Naota, Takeshi

, p. 1704 - 1706 (2005)

(Chemical Equation Presented) Highly chemoselective Baeyer-Villiger oxidations can be performed in the presence of other reactive functionalities such as alcohols, olefins, and sulfides, which would undergo electrophilic oxidation under conventional conditions (see scheme). [DMRFlEt] +[ClO4]- (depicted blue) is a new class of flavin compound that catalyzes aerobic Baeyer-Villiger oxidations in the presence of Zn dust as the electron source.

Iridium-catalyzed enantioselective allylic alkylation of methyl 2-(4-nitrophenylsulfonyl)acetate and subsequent transformations

Xu, Qing-Long,Dai, Li-Xin,You, Shu-Li

, p. 2275 - 2282 (2012)

Highly enantioselective allylic alkylation reactions of methyl 2-(4-nitrophenylsulfonyl)acetate were carried out in the presence of an iridium catalytic system. The subsequent transformations of the products including reductive desulfonylation and modifie

Acetic Acid as a Highly Reactive and Easily Separable Catalyst for the Oxidative Cleavage of Tetrahydrofuran-2-methanols to γ-Lactones

Yakura, Takayuki,Fujiwara, Tomoya,Nishi, Hideyuki,Nishimura, Yushi,Nambu, Hisanori

, p. 2316 - 2320 (2018)

[4-Iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid was developed as a highly reactive and easily separable catalyst for the oxidative cleavage of tetrahydrofuran-2-methanols to γ-lactones in the presence of Oxone (2KHSO 5 ·KHSO 4 ·K 2 SO 4) as the co-oxidant. The reactivity of this new catalyst was considerably greater than that of our previously reported catalyst, 2-iodo-N-isopropylbenzamide. The new catalyst and product were easily separated by only liquid-liquid separation without chromatography. In addition, using a mixture of nitromethane and N, N-dimethylformamide as the solvent and heating enabled a low catalyst loading, a short reaction time, and high product yield. Oxidative cleavage using the new catalyst can be used as a practical and efficient method for synthesizing γ-lactones.

Asymmetric Baeyer-Villiger oxidation with Co(Salen) and H2O 2 in water: Striking supramolecular micelles effect on catalysis

Bianchini, Giulio,Cavarzan, Alessandra,Scarso, Alessandro,Strukul, Giorgio

, p. 1517 - 1520 (2009)

A micellar environment enables catalytic, diastereoselective and enantioselective Baeyer-Villiger oxidation of cyclobutanones (ee up to 90%) with H2O2 as oxidant using Co(Salen) catalyst 1, while the same catalytic system is inactive in organic solvents. The Royal Society of Chemistry 2009.

Investigation of a New Type I Baeyer–Villiger Monooxygenase from Amycolatopsis thermoflava Revealed High Thermodynamic but Limited Kinetic Stability

Mansouri, Hamid R.,Mihovilovic, Marko D.,Rudroff, Florian

, p. 971 - 977 (2020)

Baeyer–Villiger monooxygenases (BVMOs) are remarkable biocatalysts, but, due to their low stability, their application in industry is hampered. Thus, there is a high demand to expand on the diversity and increase the stability of this class of enzyme. Sta

Design of peptide-containing: N 5-unmodified neutral flavins that catalyze aerobic oxygenations

Arakawa, Yukihiro,Yamanomoto, Ken,Kita, Hazuki,Minagawa, Keiji,Tanaka, Masami,Haraguchi, Naoki,Itsuno, Shinichi,Imada, Yasushi

, p. 5468 - 5475 (2017)

Simulation of the monooxygenation function of flavoenzyme (Fl-Enz) has been long-studied with N5-modified cationic flavins (FlEt+), but never with N5-unmodified neutral flavins (Fl) despite the fact that Fl is genuinely equal to the active center of Fl-Enz. This is because of the greater lability of 4a-hydroperoxy adduct of Fl, FlOOH, compared to those of FlEt+, FlEtOOH, and Fl-Enz, FlOOH-Enz. In this study, Fl incorporated into a short peptide, flavopeptide (Fl-Pep), was designed by a rational top-down approach using a computational method, which could stabilize the corresponding 4a-hydroperoxy adduct (FlOOH-Pep) through intramolecular hydrogen bonds. We report catalytic chemoselective sulfoxidation as well as Baeyer-Villiger oxidation by means of Fl-Pep under light-shielding and aerobic conditions, which are the first Fl-Enz-mimetic aerobic oxygenation reactions catalyzed by Fl under non-enzymatic conditions.

Silyl peroxides as effective oxidants in the Baeyer-Villiger reaction with chloroaluminate(III) ionic liquids as catalysts

Baj, Stefan,S?upska, Roksana,Chrobok, Anna,Drozdz, Agnieszka

, p. 120 - 126 (2013)

A new application of silyl peroxides as oxidants in the Baeyer-Villiger oxidation of cyclic ketones in chloroaluminate(III) ionic liquids is described. Among the silyl peroxides, the reactivity of two groups of peroxides was studied: bis(silyl) and t-butyl silyl peroxides possessing different structured substituents attached to the Si atom. It was shown that the acidic 1-hexyl-3-methylimidazolium chloroaluminate(III) ionic liquid (molar ratio of AlCl3 in ionic liquid: 0.67) present in the oxidation of cyclic ketones with bis(silyl) peroxides acts as the catalyst. In this variant of the reaction, the reactivities of bis(silyl) peroxides decrease in the following order: bis(trimethylsilyl) peroxide > bis(vinyldimethylsilyl) peroxide > bis(phenyldimethylsilyl) peroxide > bis(diphenylmethylsilyl) peroxide. A variety of cyclic ketones such as cyclobutanone, 3-substituted cyclobutanones, cyclopentanone, cyclohexanone, 2-methylcyclohexanone, 4-methylcyclohexanone, 2-adamantanone and norcamphor were oxidised to their corresponding lactones with high yields (49-100%). When t-butyl silyl peroxides and neutral chloroaluminate(III) ionic liquids (molar ratio of AlCl3 in ionic liquid: 0.5) were utilised in the Baeyer-Villiger oxidation, the studied ionic liquid acted as the reagent. Here, phenyldimethyl(t-butylperoxy)silane was the most efficient oxidant in the oxidation of cyclobutanone to γ- butyrolactone (70% yield). Other peroxides, including trimethyl(t-butylperoxy) silane, vinyldimethyl(t-butylperoxy)silane and diphenylmethyl-(t-butylperoxy) silane, were less reactive oxidants. Two variants of the Baeyer-Villiger reaction mechanism are postulated.

Dehydrogenative lactonization of diols in aqueous media catalyzed by a water-soluble iridium complex bearing a functional bipyridine ligand

Fujita, Ken-Ichi,Ito, Wataru,Yamaguchi, Ryohei

, p. 109 - 112 (2014)

A new catalytic system for the dehydrogenative lactonization of a variety of benzylic and aliphatic diols in aqueous media was developed. By using a water-soluble, dicationic iridium catalyst bearing 6,6′-dihydroxy-2, 2′-bipyridine as a functional ligand, highly atom economical and environmentally benign synthesis of various lactones was achieved in good to excellent yields. Recovery and reuse of the catalyst were also accomplished by a simple phase separation and the recovered catalyst maintained its high activity at least until the fifth run. Copyright

Asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones using a chiral cationic palladium(II) 2-(phosphinophenyl)pyridine complex as catalyst

Ito, Katsuji,Ishii, Ayako,Kuroda, Tomomi,Katsuki, Tsutomu

, p. 643 - 646 (2003)

Chiral cationic palladium(II) 2-(phosphinophenyl)pyridine (1a) complex was found to be an effective catalyst for asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones. For example, good and excellent enantioselectivities (80% and >99% ees) were

CATALYTIC REGIOSELECTIVE DEHYDROGENATION OF UNSYMMETRICAL α,ω-DIOLS USING RUTHENIUM COMPLEXES

Ishii, Youichi,Osakada, Kohtaro,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao

, p. 2677 - 2680 (1983)

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of α,β-unsaturated ketone as a hydrogen acceptor and triethylamine gave β-substituted γ-lactones and γ-substituted δ-lactones as major products, respectively.

Highly enantioselective Baeyer-Villiger oxidation using Zr(salen) complex as catalyst

Watanabe, Akira,Uchida, Tatsuya,Ito, Katsuji,Katsuki, Tsutomu

, p. 4481 - 4485 (2002)

(R,R)-Zr(salen) complex was found to serve as an efficient catalyst for asymmetric Baeyer-Villiger oxidation of pro-chiral and racemic ketones using urea·hydrogen peroxide as the terminal oxidant: for example, high enantioselectivity of 87% ee was achieve

Copper-in-charcoal (Cu/C): Heterogeneous, copper-catalyzed asymmetric hydrosilylations

Lipshutz, Bruce H.,Frieman, Bryan A.,Tomaso Jr., Anthony E.

, p. 1259 - 1264 (2006)

Asymmetric copper chemistry ... done heterogeneously? It's doable: Copper-incharcoal (Cu/C) is introduced as an easily prepared catalyst that is readily converted in situ into a nonracemically ligated form of copper hydride that effects asymmetric hydrosilylations. DTBM = 3,5-di-tert-butyl-4- methoxydiphenylphosphinyl. (Figure Presented)

Mechanistic investigation of chiral phosphoric acid catalyzed asymmetric baeyer-villiger reaction of 3-substituted cyclobutanones with H 2O2 as the oxidant

Xu, Senmiao,Wang, Zheng,Li, Yuxue,Zhang, Xumu,Wang, Haiming,Ding, Kuiling

, p. 3021 - 3035 (2010)

The mechanism of the chiral phosphoric acid catalyzed Baeyer-Villiger (B-V) reaction of cyclobutanones with hydrogen peroxide was investigated by using a combination of experimental and theoretical methods. Of the two pathways that have been proposed for the present reaction, the pathway involving a peroxyphosphate intermediate is not viable. The reaction progress kinetic analysis indicates that the reaction is partially inhibited by the y-lactone product. Initial rate measurements suggest that the reaction follows Michaelis-Menten-type kinetics consistent with a bifunctional mechanism in which the catalyst is actively involved in both carbonyl addition and the subsequent rearrangement steps through hydrogen-bonding interactions with the reactants or the intermediate. High-level quantum chemical calculations strongly support a two-step concerted mechanism in which the phosphoric acid activates the reactants or the intermediate in a synergistic manner through partial proton transfer. The catalyst simultaneously acts as a general acid, by increasing the electrophilicity of the carbonyl carbon, increases the nucleophilicity of hydrogen peroxide as a Lewis base in the addition step, and facilitates the dissociation of the OH group from the Criegee intermediate in the rearrangement step. The overall reaction is highly exothermic, and the rearrangement of the Criegee intermediate is the rate-determining step. The observed reactivity of this catalytic B-V reaction also results, in part, from the ring strain in cyclobutanones. The sense of chiral induction is rationalized by the analysis of the relative energies of the competing diastereomeric transition states, in which the steric repulsion between the 3-substituent of the cyclobutanone and the 3- and 3'-substituents of the catalyst, as well as the entropy and solvent effects, are found to be critically important.

Manipulating the stereoselectivity of the thermostable Baeyer-Villiger monooxygenase TmCHMO by directed evolution

Li, Guangyue,Fürst, Maximilian J. L. J.,Mansouri, Hamid Reza,Ressmann, Anna K.,Ilie, Adriana,Rudroff, Florian,Mihovilovic, Marko D.,Fraaije, Marco W.,Reetz, Manfred T.

, p. 9824 - 9829 (2017)

Baeyer-Villiger monooxygenases (BVMOs) and evolved mutants have been shown to be excellent biocatalysts in many stereoselective Baeyer-Villiger transformations, but industrial applications are rare which is partly due to the insufficient thermostability o

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Mukaiyama,T. et al.

, p. 1207 - 1210 (1979)

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A diastereomeric pair of sulfoxide-containing chiral MOP-type ligands: Preparation and application to rhodium-catalyzed asymmetric 1,4-addition reactions

Hoshi, Takashi,Fujita, Masataka,Matsushima, Shouta,Hagiwara, Hisahiro,Suzuki, Toshio

, p. 800 - 802 (2018)

(R,SS)-Sulfoxide-MOP (L2) and (R,RS)-sulfoxide-MOP (L3) were developed as a diastereomeric pair of sulfoxide-containing chiral MOP-type ligands. These two ligands also represent the first monosulfoxide analogues of BINAP. The chiral ligand L2 was successfully applied to the highly enantioselective rhodium-catalyzed 1,4-addition between α,β-unsaturated ketones or esters and arylboronic acids, and exhibited a broad substrate scope when the reaction was performed using 1.5 mol% Rh in cyclohexane/H2O (10:1) at 40 °C under mild basic conditions.

Construction of a new asymmetric reaction site: Asymmetric 1,4-addition of thiol using pentagonal bipyramidal Hf(salen) complex as catalyst

Matsumoto, Kazuhiro,Watanabe, Akira,Uchida, Tatsuya,Ogi, Kayoko,Katsuki, Tsutomu

, p. 2385 - 2388 (2004)

Pentagonal bipyramidal Hf(salen) complex 1 was found to serve as a catalyst for 1,4-addition reaction of thiol to N-(2-alkenoyl)-2-oxazolidinones.

Regioselective Hydrogenation of Unsymmetrically Substituted Cyclic Anhydrides Catalyzed by Ruthenium Complexes with Phosphine Ligands

Ikariya, Takao,Osakada, Kohtaro,Ishii, Youichi,Osawa, Shoichi,Saburi, Masahiko,Yoshikawa, Sadao

, p. 897 - 898 (1984)

Regioselective hydrogenation of unsymmetrically substituted cyclic anhydrides catalyzed by ruthenium complexes with mono-, di-, or triphosphine ligands produced the corresponding two isomeric lactones, where the regioselectivity was influenced by the bulkiness of substituent(s) on the anhydrides and of the phosphine ligands of catalyst.

Lactone Synthesis by α,ω-Diols with Hydrogen Peroxide Catalyzed by Heteropoly Acids Combined with Cetylpyridinium Chloride

Ishii, Yasutaka,Yoshida, Tsutomu,Yamawaki, Kazumasa,Ogawa, Masaya

, p. 5549 - 5552 (1988)

-

-

Bailey,Johnson

, p. 3574 (1970)

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Rational Construction of an Artificial Binuclear Copper Monooxygenase in a Metal-Organic Framework

Feng, Xuanyu,Song, Yang,Chen, Justin S.,Xu, Ziwan,Dunn, Soren J.,Lin, Wenbin

, p. 1107 - 1118 (2021)

Artificial enzymatic systems are extensively studied to mimic the structures and functions of their natural counterparts. However, there remains a significant gap between structural modeling and catalytic activity in these artificial systems. Herein we report a novel strategy for the construction of an artificial binuclear copper monooxygenase starting from a Ti metal-organic framework (MOF). The deprotonation of the hydroxide groups on the secondary building units (SBUs) of MIL-125(Ti) (MIL = Matériaux de l'Institut Lavoisier) allows for the metalation of the SBUs with closely spaced CuI pairs, which are oxidized by molecular O2 to afford the CuII2(μ2-OH)2 cofactor in the MOF-based artificial binuclear monooxygenase Ti8-Cu2. An artificial mononuclear Cu monooxygenase Ti8-Cu1 was also prepared for comparison. The MOF-based monooxygenases were characterized by a combination of thermogravimetric analysis, inductively coupled plasma-mass spectrometry, X-ray absorption spectroscopy, Fourier-transform infrared spectroscopy, and UV-vis spectroscopy. In the presence of coreductants, Ti8-Cu2 exhibited outstanding catalytic activity toward a wide range of monooxygenation processes, including epoxidation, hydroxylation, Baeyer-Villiger oxidation, and sulfoxidation, with turnover numbers of up to 3450. Ti8-Cu2 showed a turnover frequency at least 17 times higher than that of Ti8-Cu1. Density functional theory calculations revealed O2 activation as the rate-limiting step in the monooxygenation processes. Computational studies further showed that the Cu2 sites in Ti8-Cu2 cooperatively stabilized the Cu-O2 adduct for O-O bond cleavage with 6.6 kcal/mol smaller free energy increase than that of the mononuclear Cu sites in Ti8-Cu1, accounting for the significantly higher catalytic activity of Ti8-Cu2 over Ti8-Cu1.

Efficient Oxidative Cleavage of Tetrahydrofuran-2-methanols to γ-Lactones by a 2-Iodobenzamide Catalyst in Combination with Oxone

Yakura, Takayuki,Horiuchi, Yuto,Nishimura, Yushi,Yamada, Akihiro,Nambu, Hisanori,Fujiwara, Tomoya

, p. 869 - 873 (2016)

An environmentally friendly oxidative cleavage of tetrahydrofuran-2-methanols to the corresponding γ-lactones using a catalytic amount of 2-iodo-N-isopropylbenzamide has been developed. The reaction of various tetrahydrofuran-2-methanols with the catalyst in the presence of Oxone (2 KHSO5·KHSO4·K2SO4) as a co-oxidant in DMF at room temperature successfully affords the corresponding lactones in good to high yields, and recovery of the catalyst is readily accomplished using a reductive work-up. This method is notable because it enables the transformation of tetrahydrofuran-2-methanols to γ-lactones under mild conditions without the use of any toxic heavy metals.

The rationale for stereoinduction in conjugate addition to alkylidenemalonates bearing a menthol-derived chiral auxiliary

Yamada, Ken-ichi,Fujiwara, Shinichi,Inokuma, Tsubasa,Sugano, Masayuki,Yamaoka, Yousuke,Takasu, Kiyosei

, (2021)

Density-functional theory (DFT) calculations provided a new model to rationalize the stereoselectivity in the asymmetric addition to alkylidenemalonate bearing 8-phenylmenthyl groups as a chiral auxiliary. The diastereoselectivity in the addition reactions of a tetramethyldioxolanyl radical with various alkyl 8-phenylmenthyl benzylidenemalonates strongly supports the proposed model.

Parallel kinetic resolutions of monosubstituted succinic anhydrides catalyzed by a modified cinchona alkaloid [7]

Chen,Deng

, p. 11302 - 11303 (2001)

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Pyrazinium salts as efficient organocatalysts of mild oxidations with hydrogen peroxide

Menova, Petra,Kafka, Frantisek,Dvorakova, Hana,Gunnoo, Smita,Sanda, Miloslav,Cibulka, Radek

, p. 865 - 870 (2011)

A series of 3-substituted pyrazinium tetrafluoroborates was prepared as simple analogues of flavinium salts which are efficient organocatalysts for oxidations with hydrogen peroxide. It was shown that pyrazinium derivatives with an electron-withdrawing su

Direct Organocatalytic Multicomponent Synthesis of Enantiopure γ-Butyrolactones via Tandem Knoevenagel-Michael-Lactonization Sequence

Khopade, Tushar M.,Sonawane, Amol D.,Arora, Jyotsna S.,Bhat, Ramakrishna G.

, p. 3905 - 3910 (2017)

An expedient and straightforward protocol is developed for the synthesis of highly enantiopure synthesis of γ-butyrolactones. For the first time, one pot enantioselective organocatalytic multicomponent reaction (OMCR) is explored to construct functionalized butyrolactones without the use of pre-functionalized substrates and expensive transition metals. The protocol is proved to be reproducible on a gram scale. Density functional theory (DFT) calculations strongly support the mechanism and were in close agreement with the observed high stereoselectivity. (Figure presented.).

Influence of hydroperoxides on the enantioselectivity of metal-catalyzed asymmetric Baeyer-Villiger oxidation and epoxidation with chiral ligands

Bolm, Carsten,Beckmann, Oliver,Kuehn, Toralf,Palazzi, Chiara,Adam, Waldemar,Rao, Paraselli Bheema,Saha-Moeller, Chantu R.

, p. 2441 - 2446 (2001)

Chiral hydroperoxides have a significant influence on the enantioselectivity of the metal-catalyzed asymmetric Baeyer-Villiger oxidation of cyclic ketones and the epoxidation of allylic alcohols, when chiral ligands are employed. If both the ligand and th

Ruthenium Complex Catalyzed Regioselective Dehydrogenation of Unsymmetrical α,ω-Diols

Ishii, Youichi,Osakada, Kohtaro,Ikariya, Takao,Saburi, Masahiko,Yoshikawa, Sadao

, p. 2034 - 2039 (1986)

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of such a hydrogen acceptor as α,β-unsaturated ketone gave predominantly β-substituted γ-lactones and γ-substituted δ-lactones, respectively.Among the ruthenium complexes, RuH2(PPh3)4 was the most active and selective catalyst and showed high catalytic activity even at 20 deg C.For example, 2,2-dimethyl-1,4-butanediol was quantitatively converted to dihydro-4,4-dimethyl-2(3H)-furanone and dihydro-3,3-dimethyl-2(3H)-furanone in a ratio of 99.6/0.4 in the presence of 4-phenyl-3-buten-2-one (hydrogen acceptor) and a catalytic amount of RuH2(PPh3)4 at 20 deg C.The proposed main factor controlling the regioselectivity is the steric constraints produced by the substituent(s) of a diol at the coordination step of alkoxy group to ruthenium.

(R)-3,5-diCF3-SYNPHOS and (R)- p -CF3-SYNPHOS, electron-poor diphosphines for efficient room temperature Rh-catalyzed asymmetric conjugate addition of arylboronic acids

Berhal, Farouk,Esseiva, Olivier,Martin, Charles-Henri,Tone, Hitoshi,Genet, Jean-Pierre,Ayad, Tahar,Ratovelomanana-Vidal, Virginie

, p. 2806 - 2809 (2011)

Two new atropisomeric electron-poor chiral diphosphine ligand analogues of SYNPHOS were prepared, and their electronic properties are described. These two ligands afforded high performance for the Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds at room temperature.

Aerobic lactonization of diols by biomimetic oxidation

Endo, Yoshinori,Baeckvall, Jan-E.

, p. 12596 - 12601 (2011)

Coming up for air: Highly efficient aerobic lactonization can be carried out by a biomimetic oxidation system based on coupled redox catalysts (ruthenium catalyst and electron transfer mediators). This system leads to a low-energy electron transfer from diol to molecular oxygen. Various diols were aerobically oxidized to the corresponding five- to nine-membered lactones in good to high yields under mild reaction conditions (see scheme).

Asymmetric 1,4-hydrosilylations of α,β-unsaturated esters

Lipshutz, Bruce H.,Servesko, Jeff M.,Taft, Benjamin R.

, p. 8352 - 8353 (2004)

Complexing catalytic amounts of CuH with a nonracemic JOSIPHOS or SEGPHOS ligand, together with stoichiometric PMHS, leads to exceedingly efficient and highly enantioselective 1,4-reductions of β,β-disubstituted enoates and lactones. An unprecedented subs

The steroid monooxygenase from Rhodococcus rhodochrous; A versatile biocatalyst

Leipold, Friedemann,Rudroff, Florian,Mihovilovic, Marko D.,Bornscheuer, Uwe T.

, p. 1620 - 1624 (2013)

The substrate scope of a steroid monooxygenase (STMO) from Rhodococcus rhodochrous DSM 43269 was investigated for a large range of different ketone substrates. These studies revealed that this enzyme not only oxygenates steroids, but also ketone moieties of a series of other open-chain ketones, such as cyclohexyl methyl ketone, cyclopentyl methyl ketone, and 3-acetylindole. Furthermore, the STMO catalyzed the oxygenation of cyclobutanone derivatives. Comparative biotransformations with recombinant Escherichia coli resting cells harboring the STMO, the cycloalkanone monooxygenase (CAMO) from Cylindrocarpon radicicola or the cyclohexanone monooxygenase (CHMO) from Acinetobacter calcoaceticus revealed that the STMO is enantiodivergent compared to the CHMO-type. Moreover, the STMO resulted in a higher enantiomeric excess of the product lactones compared to the known BVMOs of the same enantiopreference, such as cyclopentanone monooxygenases.

Enantiomerically pure rhodium complexes bearing 1,5-diphenyl-1,5- cyclooctadiene as a chiral diene ligand. Their use as catalysts for asymmetric 1,4-addition of phenylzinc chloride

Kina, Asato,Ueyama, Kazuhito,Hayashi, Tamio

, p. 5889 - 5892 (2005)

(Chemical Equation Presented) A rhodium complex coordinated with 1,5-diphenyl-1,5-cyclooctadiene (Ph-cod), [RhCl((R)-Ph-cod)]2, was obtained enantiomerically pure through optical resolution of diastereomeric isomers [Rh(Ph-cod)((R)-1,1′-binapht

ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED γ-BUTYROLACTONES

Mukaiyama, Teruaki,Fujimoto, Katsumi,Hirose, Takuji,Takeda, Takeshi

, p. 635 - 638 (1980)

Highly optically pure β-substituted γ-butyrolactones (V) were obtained in good yields by the reaction of (E)-(2R,3S)-6-alkylidene-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione (I) with phenylthiomethyllithium, followed by i) treatment with trimethyloxonium tetrafluoroborate and ii) acid hydrolysis.

Enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes

Kurihara, Kazunori,Sugishita, Noriyuki,Oshita, Kengo,Piao, Dongguo,Yamamoto, Yasunori,Miyaura, Norio

, p. 428 - 435 (2007)

A chiral bidentate phosphoramidite (5a) was synthesized from Shibasaki's linked-(R)-BINOL and P(NMe2)3 as a new ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds. The effects of 5a and Feringa's monodentate phosphoramidite (4, R1, R2 = Et) on the yields and enantioselectivities were fully investigated. The reaction was significantly accelerated in the presence of a base such as KOH and Et3N, allowing the reaction to be completed at the lower temperatures than 50 °C. The addition to cyclic enones such as 2-cyclopentenone, 2-cyclohexenone and 2-cycloheptenone at 50 °C in the presence of an [Rh(coe)2Cl]2-4 (R1, R2 = Et) complex resulted in enantioselectivities up to 98%, though it was less effective for acyclic enones (0-70% ee). On the other hand, a complex between [Rh(nbd)2]BF4 and 5a completed the addition to cyclic enones within 2 h at room temperature in the presence of Et3N with 86-99% yields and 96-99.8% ee. This catalyst was also effective for acyclic enones, resulting in 62-98% yields and 66-94% ee. The 1,4-additions of arylboronic acids to unsaturated lactones and acyclic esters with rhodium(I)-phosphoramidites complexes were also investigated.

-

Russell,VanderWerf

, p. 11 (1947)

-

The mutagenesis of a single site for enhancing or reversing the enantio- or regiopreference of cyclohexanone monooxygenases

Hu, Yujing,Xu, Weihua,Hui, Chenggong,Xu, Jian,Huang, Meilan,Lin, Xianfu,Wu, Qi

, p. 9356 - 9359 (2020)

The mutagenesis of a "second sphere"switch residue of CHMOAcineto could control its enantio- and regiopreference. Replacing phenylalanine (F) at position 277 of CHMOAcineto into larger tryptophan (W) enabled a significant enhancement of enantio- or regioselectivity toward structurally diverse substrates, moreover, a complete reversal of enantio- or regiopreference was realized by mutating F277 into a range of smaller amino acids (A/C/D/E/G/H/I/K/L/M/N/P/Q/R/S/T/V).

Self-assembled ion-pair organocatalysis - Asymmetric Baeyer-Villiger oxidation mediated by flavinium-cinchona alkaloid dimer

Poudel, Pramod Prasad,Arimitsu, Kenji,Yamamoto, Kana

, p. 4163 - 4166 (2016)

An ion-pair catalyst generated by assembly of a chiral flavinium and a cinchona alkaloid dimer for use in asymmetric Baeyer-Villiger oxidation is presented. Ion-pair formation is essential for enhancing the catalytic activity and stereoselectivity. The catalyst is applicable to structurally diverse 3-substituted cyclobutanones, providing good to excellent enantioselectivities (up to 98: 2 e.r.). This study provides the first example of self-assembly of a flavin derivative and a base to form a chiral reaction site that enables a highly stereoselective reaction to occur.

Phosphothreonine (pThr)-Based Multifunctional Peptide Catalysis for Asymmetric Baeyer-Villiger Oxidations of Cyclobutanones

Featherston, Aaron L.,Shugrue, Christopher R.,Mercado, Brandon Q.,Miller, Scott J.

, p. 242 - 252 (2019)

Biologically inspired phosphothreonine (pThr)-embedded peptides that function as chiral Br?nsted acid catalysts for enantioselective Baeyer-Villiger oxidations (BV) of cyclobutanones with aqueous H2O2 are reported herein. Complementa

Enantioselective Metal-catalyzed Baeyer-Villiger Oxidation of Cyclobutanones

Bolm, Carsten,Luong, T. Kim Khanh,Schlingloff, Gunther

, p. 1151 - 1152 (1997)

Optically active lactones are obtained by metal-catalyzed aerobic oxidation of prochiral cyclobutanones. Starting from 3-mono-substituted substrates lactones with moderate enantioselectivities (up to 47% ee) have been obtained. Kelly's tricyclic ketone 8

Chiral Bronsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2

Xu, Senmiao,Wang, Zheng,Zhang, Xue,Zhang, Xumu,Ding, Kuiling

, p. 2840 - 2843 (2008)

(Chemical Equation Presented) A catalytic amount of a chiral Bronsted acid with aqueous H2O2 as the oxidant is sufficient for the enantioselective Baeyer-Villiger oxidation of 3-substituted cyclobutanones to give the corresponding γ-

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen

Ban, Kazuho,Sajiki, Hironao,Sawama, Yoshinari,Takakura, Ryoya

, p. 1919 - 1923 (2019)

A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.

Vaulted biaryls: Efficient ligands for the aluminum-catalyzed asymmetric baeyer-villiger reaction

Bolm, Carsten,Frison, Jean-Cédric,Zhang, Yu,Wulff, William D.

, p. 1619 - 1621 (2004)

Vaulted biaryls (VANOL and VAPOL) have been applied in the aluminum-catalyzed asymmetric Baeyer-Villiger reaction of prochiral 3-substituted cyclobutanones. Optically active γ-butyrolactones are obtained in high yields with enantioselectivities of up to 84% ee.

Chemo-enzymatic Baeyer-Villiger oxidation in the presence of Candida antarctica lipase B and ionic liquids

Drozdz, Agnieszka,Erfurt, Karol,Bielas, Rafal,Chrobok, Anna

, p. 1315 - 1321 (2015)

A new method for the chemo-enzymatic Baeyer-Villiger oxidation of cyclic ketones to lactones has been developed. The influence of reaction parameters and the structure of various ionic liquids were studied. Free Candida antarctica lipase B or Novozyme-435 suspended in an ionic liquid was used as the catalytic phase. The reaction was carried out under mild conditions at room temperature using 30% aq. H2O2 as the oxidation agent. 1-Butyl-3-methyl bistriflimide was the most effective ionic liquid and increased the reaction rate compared to toluene. Lipase exhibited good stability, and the ionic liquid could be easily reused. Therefore, a general chemo-enzymatic method for the oxidation of cyclohexanones and cyclobutanones to obtain adequate lactones in high yields (79-95%) has been proposed.

Regioselectivity in Nickel(II)-Mediated Oxidations of Diols

Doyle, Michael P.,Dow, Robert L.,Bagheri, Vahid,Patrie, William, J.

, p. 476 - 480 (1983)

Oxidations of 2- and 4-substituted 1,4-butanediols to their corresponding γ-butyrolactones by the combination of molecular bromine and nickel(II) alkanoate occur with a high degree of regioselectivity.The influence of the alkanoate ligand, of substituents at the 2-position of 1,4-butanediols, and of solvent on oxidation regiocontrol is examined, and comparison of regioselectivity in diol oxidations is made with representative conventional oxidative methods.Regiocontrol in nickel(II)-mediated reactions is proposed to be derived from steric constraints for oxidativehydrogen transfer to the alkanoate ligand of nickel(II) in the diol-associated complex.Alternate use of cobalt(II) alkanoates provides regiocontrol in diol oxidations that is comparable or superior to that obtained with nickel(II) alkanoates in bromine oxidations.

Family clustering of Baeyer-Villiger monooxygenases based on protein sequence and stereopreference

Mihovilovic, Marko D.,Rudroff, Florian,Groetzl, Birgit,Kapitan, Peter,Snajdrova, Radka,Rydz, Joanna,Mach, Robert

, p. 3609 - 3613 (2005)

(Chemical Equation Presented) The identification of enzyme pairs with overlapping substrate specificity and enantiocomplementary transformations is a key challenge in biocatalysis. Enantio and regiodivergent Baeyer-Villiger oxidations were successfully carried out by using a small library of recombinant Escherichia coli strains expressing monooxygenases of various microbial origin (see picture). The clustering of enzymes based on stereopreference is in good agreement with phylogenetic similarity.

Catalytic Asymmetric Conjugate Addition of a Borylalkyl Copper Complex for Chiral Organoboronate Synthesis

Jang, Won Jun,Yun, Jaesook

, p. 18131 - 18135 (2019)

We report the catalytic enantioselective conjugate addition of a borylalkyl copper nucleophile generated in situ from a 1,1-diborylmethane derivative to α,β-unsaturated diesters. In the presence of a chiral N-heterocyclic carbene (NHC)–copper catalyst, this method facilitated the enantioselective incorporation of a CH2Bpin moiety at the β-position of the diesters to yield β-chiral alkyl boronates in up to 86 % yield with high enantioselectivity. The alkylboron moiety in the resulting chiral diester products was converted into various functional groups by organic transformation of the C?B bond.

Asymmetric Baeyer-Villiger reaction: Diastereodifferentiating peracid oxidation of chiral acetal in the presence of Lewis acid

Sugimura, Takashi,Fujiwara, Yoshihisa,Akira, Tai

, p. 6019 - 6022 (1997)

Oxidation of 2 with m-chloroperbenzoic acid in the presence of SnCl4 at -78°C followed by hydrolysis afforded optically active 4 in a quantitative yield. The enantiomeric excess tee) of 4 largely depended on the reaction solvent, the chiral dio

Enantioselective Baeyer-Villiger oxidations catalyzed by chiral magnesium complexes

Bolm,Beckmann,Cosp,Palazzi

, p. 1461 - 1463 (2001)

Catalytic enantioselective Baeyer-Villiger oxidations of 3-substituted cyclobutanones with cumene hydroperoxide as oxidant have successfully been performed in the presence of chiral magnesium catalysts. The combination of enantiopure BINOL and a variety o

Chemo-enzymatic Baeyer-Villiger oxidation of 4-methylcyclohexanone via kinetic resolution of racemic carboxylic acids: Direct access to enantioenriched lactone

Drozdz, Agnieszka,Chrobok, Anna

, p. 1230 - 1233 (2016)

A new method for the asymmetric chemo-enzymatic Baeyer-Villiger oxidation of prochiral 4-methylcyclohexanone to (R)-4-methylcaprolactone in the presence of (±)-4-methyloctanoic acid, Candida Antarctica lipase B and 30% aq. H2O2 has been developed. A mechanism for the asymmetric induction based on kinetic resolution of racemic carboxylic acids is proposed.

Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step

Chan, Wei Chuen,Vinod, Jincy K.,Koide, Kazunori

, p. 3674 - 3682 (2021/02/16)

We describe a visible-light-promoted addition of a hydrogen atom and an acetal carbon toward various electron-deficient alkenes. 1,3-Dioxolane is converted to its radical species in the presence of persulfate and an iridium catalyst upon visible light irradiation, which then reacts with electron-deficient alkenes. The reaction operates via a radical chain mechanism, a less commonly observed pathway for this class of transformation. Hydrogen atom transfer from 1,3-dioxolane to α-malonyl radicals is corroborated by experimental and density functional theory studies.

Process route upstream and downstream products

Process route

4-phenyl-5H-furan-2-one
1575-47-9

4-phenyl-5H-furan-2-one

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7,68844-05-3,93601-84-4,68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

Conditions
Conditions Yield
With polymethylhydrosiloxane; (triphenylphosphine)copper(I) hydride hexamer; (R)-(-)-DTBM-SEGPHOS; tert-butyl alcohol; In tetrahydrofuran; at 0 ℃; for 2h;
96%
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; polymethylhydrosiloxane; copper diacetate; In tetrahydrofuran; tert-butyl alcohol; at 80 ℃; for 0.5h; microwave irradiation;
93%
With (R)-(-)-DTBM-SEGPHOS; sodium phenoxide; poly(methylhydrosiloxane); copper carbide; In toluene; tert-butyl alcohol; at 20 ℃; for 7h;
82.5%
With [Ir(C8H12)((o-tol)2PC6H9NC3H3NOCH(CH3)2)]BArF; hydrogen; In dichloromethane; at 20 ℃; for 24h; under 75007.5 Torr; optical yield given as %ee; enantioselective reaction;
2-hydroxymethyl-4-phenyltetrahydrofuran

2-hydroxymethyl-4-phenyltetrahydrofuran

4-phenyldihydrofuran-2(3H)-one
1008-73-7

4-phenyldihydrofuran-2(3H)-one

Conditions
Conditions Yield
With Oxone; [4-iodo-3-(isopropylcarbamoyl)phenoxy]acetic acid; In nitromethane; N,N-dimethyl-formamide; at 20 - 50 ℃; for 8h; Reagent/catalyst; Temperature;
85%
With oxone; N-isopropyl-2-iodobenzamide; In N,N-dimethyl-formamide; at 20 ℃; for 22h;
70%
phenylzinc chloride
28557-00-8

phenylzinc chloride

2-buten-4-olide
497-23-4

2-buten-4-olide

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7,68844-05-3,93601-84-4,68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

Conditions
Conditions Yield
phenylzinc chloride; 2-buten-4-olide; With chloro-trimethyl-silane; [Rh((R)-Pd-cod)((R)-1,1'-binaphthyl-2,2'-diamine)]BF4; In tetrahydrofuran; at 30 ℃; for 1h;
With hydrogenchloride;
86%
4-phenyl-5H-furan-2-one
1575-47-9

4-phenyl-5H-furan-2-one

4-phenyldihydrofuran-2(3H)-one
1008-73-7

4-phenyldihydrofuran-2(3H)-one

Conditions
Conditions Yield
With palladium 10% on activated carbon; hydrogen; In methanol; under 1500.15 Torr;
100%
With hydrogen; palladium on activated charcoal; In ethyl acetate;
96%
With hydrogen; palladium on activated charcoal; In methanol; for 4h;
With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 3h; Inert atmosphere;
2-buten-4-olide
497-23-4

2-buten-4-olide

phenylboronic acid
98-80-6

phenylboronic acid

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7,68844-05-3,93601-84-4,68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

4-phenyldihydrofuran-2-one
68844-05-3

4-phenyldihydrofuran-2-one

Conditions
Conditions Yield
With potassium hydroxide; R,R,R-5-All-3-iBu-8-MeO-1,8-Me2bicyclo[2.2.2]octa-2,5-diene; Rh(H2C=CH2)2Cl; In 1,4-dioxane; water; at 25 ℃; Title compound not separated from byproducts;
With triethylamine; [Rh(ndb)2]BF4; (R)-BINOL-based bidentate phosphoramidite; In 1,4-dioxane; water; at 25 ℃; for 6h; Title compound not separated from byproducts.;
With potassium hydroxide; C4H8Cl2Rh; (1S,4R,8R)-8-methoxy-2-(4-methoxyphenyl)-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene; In methanol; dichloromethane; at 20 ℃; for 1h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
With chlorobis(ethylene)rhodium(I) dimer; (R)-[6,6'-bis(bis(3,5-di(trifluoromethyl)phenyl)phosphino)-2,2',3,3'-tetrahydro-5,5'-bibenzo[b][1,4]dioxine]; potassium hydroxide; In water; toluene; at 20 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
With chlorobis(ethylene)rhodium(I) dimer; (R)-3,4,5-triF-SYNPHOS; potassium hydroxide; In water; toluene; at 20 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
With acetylacetonatobis(ethylene)rhodium(I); C27H25FeP; In 1,4-dioxane; water; at 100 ℃; for 18h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)propanoate

methyl 3-phenyl-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)propanoate

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7,68844-05-3,93601-84-4,68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

4-phenyldihydrofuran-2-one
68844-05-3

4-phenyldihydrofuran-2-one

Conditions
Conditions Yield
With triethylsilane; trifluoroacetic acid; for 4h; optical yield given as %ee; Reflux;
With triethylsilane; In trifluoroacetic acid; at 90 ℃; for 4h; Overall yield = 100 percent; Overall yield = 6.3 mg;
(±)-5-methyl-2-phenylhex-4-en-1-ol

(±)-5-methyl-2-phenylhex-4-en-1-ol

4-phenyldihydrofuran-2(3H)-one
1008-73-7

4-phenyldihydrofuran-2(3H)-one

trans-2-(1-hydroxy-1-metzhylethyl)-4-phenyltetrahydrofuran

trans-2-(1-hydroxy-1-metzhylethyl)-4-phenyltetrahydrofuran

cis-2-(4-phenyltetrahydrofuran-2-yl)propan-2-ol

cis-2-(4-phenyltetrahydrofuran-2-yl)propan-2-ol

Conditions
Conditions Yield
With tert.-butylhydroperoxide; V(5+)*C2H5O(1-)*O(2-)*C2H6O*C13H9NO2(2-); In nonane; ethanol; chloroform; at 20 ℃; for 72h;
78 % de
6%
4-Phenyltetrahydrofuran-2-ol
128372-48-5

4-Phenyltetrahydrofuran-2-ol

4-phenyldihydrofuran-2(3H)-one
1008-73-7

4-phenyldihydrofuran-2(3H)-one

Conditions
Conditions Yield
With Celite; silver carbonate; In toluene; at 80 ℃; for 0.5h;
93%
With silver carbonate; In toluene; at 90 ℃; for 8h;
55%
trimethyl(phenyl)stannane
934-56-5

trimethyl(phenyl)stannane

2-buten-4-olide
497-23-4

2-buten-4-olide

4-phenyldihydrofuran-2(3H)-one
1008-73-7

4-phenyldihydrofuran-2(3H)-one

Conditions
Conditions Yield
With water; bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; at 60 ℃;
68%
4-phenyl-5H-furan-2-one
1575-47-9

4-phenyl-5H-furan-2-one

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7,68844-05-3,93601-84-4,68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

4-phenyldihydrofuran-2-one
68844-05-3

4-phenyldihydrofuran-2-one

Conditions
Conditions Yield
With 1,1′-binaphthalene-2,2′-diylbis[bis(4-methylphenyl)phosphine]; sodium t-butanolate; isopropyl alcohol; In dichloromethane; toluene; pentane; at -20 ℃; for 7h; Title compound not separated from byproducts;

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