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Cas Database

100018-61-9

100018-61-9

Identification

  • Product Name:(R)-2-methyl-2-phenyloxirane

  • CAS Number: 100018-61-9

  • EINECS:

  • Molecular Weight:134.178

  • Molecular Formula:C9H10O

  • HS Code:

  • Mol File:100018-61-9.mol

Synonyms:

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    Relevant articles and documentsAll total 106 Articles be found

    Immobilization of (tartrate-salen)Mn(III) polymer complexes into SBA-15 for catalytic asymmetric epoxidation of alkenes

    Jia, Yihong,ALOthman, Zeid A.,Liang, Rui,Cha, Shuangshuang,Li, Xiaoyong,Ouyang, Weiyi,Zheng, Aqun,Osman, Sameh M.,Luque, Rafael,Sun, Yang

    , (2020/08/19)

    A series of (tartrate-salen)Mn(III) polymer complexes were prepared and immobilized into SBA-15, being subsequently employed as catalysts in the asymmetric epoxidation of alkenes. 1H NMR, FT-IR, UV–vis, elemental analysis, GPC and ICP-AES demonstrated the successful synthesis of polymer complexes, while powdered XRD, nitrogen physisorption and XPS studies proved the immobilization of polymer complexes into SBA-15. Both homogeneous and heterogeneous catalysis revealed that configurations of major epoxide products were still determined by salen chirality but e.e. values could be improved when tartrate and salen were configurationally identical. Combinations of (R,R)-salen with (R,R)-tartrate usually offered higher enantioselectivities. SBA-15 was satisfactory supporting material due to the high enantioselectivities and recycling yields obtained. The synthesized SBA-15-supported (tartrate-salen)Mn(III) catalysts showed continuous high enantioselectivities for epoxidation of α-methylstyrene, indicating great prospects for large-scale production.

    Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

    Berijani, Kayhaneh,Morsali, Ali

    , p. 206 - 218 (2021/01/11)

    Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.

    Chirally-Modified Graphite Oxide as Chirality Inducing Support for Asymmetric Epoxidation of Olefins with Grafted Manganese Porphyrin

    Ahadi, Elahe,Hosseini-Monfared, Hassan,Schlüsener, Carsten,Janiak, Christoph,Farokhi, Afsaneh

    , p. 861 - 873 (2019/11/03)

    Abstract: A chirality inducer was prepared by graphite oxide (GO) functionalization with enantiopure l-tartrate (GO*) and used as asymmetric support for a covalently-linked manganese porphyrine complex [Mn(TPyP)OAc]. The thereby obtained heterogeneous catalyst, GO*-[Mn(TPyP)OAc], showed excellent performance and ee-values of 92–99% for the asymmetric epoxidation of prochiral olefins with O2 as oxidant and isobutyraldehyde as co-reductant in acetonitrile; linear terminal olefins with 54–76% conversion and quantitative conversion of aromatic olefins. The GO*-[Mn(TPyP)OAc] catalyst is highly active, recyclable, and at the same time simple and inexpensive to prepare with a chiral inducer from the chiral pool. The structure of the catalyst was elucidated by scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET analysis,?FT-IR, Raman, and photoluminescence spectroscopic methods. Graphic Abstract: Graphite oxide functionalized with an enantiopure group was used as a chirality inducer and asymmetric support for a Mn-porphyrine complex. The thereby obtained heterogeneous catalyst is an excellent enantioselective catalyst for the epoxidation of prochiral olefins.[Figure not available: see fulltext.].

    Chiral porous poly(ionic liquid)s: Facile one-pot, one-step synthesis and efficient heterogeneous catalysts for asymmetric epoxidation of olefins

    Tian, Yabing,Wang, Jixia,Zhang, Shiguo,Zhang, Yan

    , (2022/01/26)

    Ionic liquids are potential media/solvents for asymmetric synthesis when combined with chiral catalysts, while most reported catalysts are homogenous, making them difficult to separate from the reaction systems. Herein, chiral porous poly(ionic liquid)s (

    Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

    Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk

    , p. 5077 - 5085 (2021/08/16)

    Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

    Process route upstream and downstream products

    Process route

    Conditions
    ConditionsYield
    With iron oxide; oxygen; isobutyraldehyde;Inacetonitrile;at 25 ℃; for 8h; under 750.075 Torr;
    8 %Chromat.
    20 %Chromat.
    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    benzaldehyde
    100-52-7

    benzaldehyde

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With oxygen; isobutyraldehyde;Inacetonitrile;at 45 ℃; for 8h; Reagent/catalyst; enantioselective reaction;
    77%
    8%
    15%
    With oxygen; isobutyraldehyde;Inacetonitrile;at 40 ℃; for 2h; under 750.075 Torr; enantioselective reaction;
    35 %Chromat.
    30 %Chromat.
    35 %Chromat.
    With oxygen; isobutyraldehyde;Inacetonitrile;at 45 ℃; for 4h; enantioselective reaction; Catalytic behavior;
    74 % ee
    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    acetophenone
    98-86-2

    acetophenone

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With oxygen; isobutyraldehyde;Inacetonitrile;at 25 ℃; for 8h; enantioselective reaction;
    53%
    33%
    14%
    With L-Tartaric acid; iron(III) chloride hexahydrate; oxygen; isobutyraldehyde;Inacetonitrile;at 20 ℃; for 7h; under 1500.15 Torr; Optical yield = 5 %ee; Autoclave;
    26 %Chromat.
    With oxygen; isobutyraldehyde;Inacetonitrile;at 25 ℃; for 4h; enantioselective reaction; Catalytic behavior; Green chemistry;
    71 % ee
    10 %Chromat.
    2-methyl-2-phenyloxirane
    2085-88-3

    2-methyl-2-phenyloxirane

    (2S)-2-phenylpropane-1,2-diol
    2406-22-6

    (2S)-2-phenylpropane-1,2-diol

    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With Aspergillus niger LCP 521 epoxide hydrolase;InN,N-dimethyl-formamide;at 27 ℃; pH=8.0; Further Variations:; Reagents; Product distribution;
    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With C26H36F6FeN6O6S2; C30H44N4O8; dihydrogen peroxide;Inwater; acetonitrile;at -30 ℃; for 0.5h; Reagent/catalyst; enantioselective reaction;
    80%
    With sodium hypochlorite; chloro-<5,10,15,20-tetrakis<(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-yl>porphirinato>manganese(III); t-BuPy; tetradecyl benzyl dimethyl ammonium chloride;Indichloromethane;for 1h; Product distribution; Ambient temperature;
    With Oxone; C6H10O6(C3H4)2; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; sodium hydrogencarbonate;Inwater; acetonitrile;at -10 ℃; for 1.5h; Product distribution; other reaction time, solvent, reagent;
    With Antifoam A; dihydrogen peroxide; sodium citrate;Inacetone;for 0.75h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; chloroperoxidase from the fungus Caldariomyces fumago;
    With lithium hypochlorite; benzyldimethyltetradecylammonium chloride; 1,5-dicyclohexyl imidazole; chloromanganese porphyrin (C100H108N4)MnCl;Indichloromethane;at 0 - 5 ℃; Title compound not separated from byproducts;
    With Oxone; AcOCH2C6H6O4(C3H6)2; potassium carbonate; acetic acid;In1,2-dimethoxyethane;at -10 ℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
    With N-methyl-2-indolinone; 3-chloro-benzenecarboperoxoic acid; chiral salen Mn(III) complex immobilized on MCM41;Indichloromethane;at -78 ℃; for 4h;
    With N-methyl-2-indolinone; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]](2-)-N,N',O,O'-manganese;Indichloromethane;at -78 ℃; Title compound not separated from byproducts;
    With osmium(VIII) oxide; N-methyl-2-indolinone; quinine-based chiral ligand;Inwater; acetone;at 0 ℃; for 10h; Title compound not separated from byproducts;
    With sodium hypochlorite; chiral polystyrene-PhSO3-Mn(salen) derivative;Indichloromethane;at 20 ℃; for 24h; Further Variations:; Reagents; Product distribution;
    With sodium hypochlorite; (S,S)-Mn(salen); silica gel;Indichloromethane;at 20 ℃; for 24h; pH=11.3; Further Variations:; Catalysts; time; Product distribution;
    With 3-oxo-12α-(OCOCO2H)-5β-cholan-24-oic acid methyl ester; Oxone; sodium hydrogencarbonate;Inwater; acetonitrile;for 12h; Title compound not separated from byproducts;
    With pyridine N-oxide; sodium hypochlorite; water; salen-Mn(III);Indichloromethane;at 0 ℃; for 10h; Further Variations:; Catalysts; Temperatures; Product distribution;
    With Di(2-ethylhexyl)phthalate; recombinant E. coli JM101 (pSPZ10); styrene monooxygenase; magnesium sulfate;Inoctane; water;at 30 ℃; for 23.5h; pH=7.1; Title compound not separated from byproducts.; Enzymatic reaction;
    With urea-hydrogen peroxide;In1,2-dichloro-ethane;at 40 ℃; for 40h; Title compound not separated from byproducts.;
    With oxone; ethylenediaminetetraacetic acid; C18H21NO6; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; acetic acid;In1,4-dioxane; water;at -10 ℃; for 2h; pH=9.3; optical yield given as %ee;
    With C46H50Cl4Fe2N6O; dihydrogen peroxide; acetic acid;Inwater; acetonitrile;at 20 ℃; for 0.05h; optical yield given as %ee;
    With (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4.5]decane-8,9-diyl diacetate; Oxone; ethylenediaminetetraacetic acid; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate;InDimethoxymethane; water; acetonitrile;at 0 ℃; for 8h; pH=7.0; optical yield given as %ee; aq. phosphate buffer;
    With Oxone; 18-crown-6 ether; C28H36N(1+)*F6Sb(1-); sodium hydrogencarbonate;Indichloromethane; water;at 0 ℃; enantioselective reaction;
    With sodium hypochlorite; AuCl2((C6H5)(C3H3NO)(C5H3N)C(O)NCH(C6H5)CH2OH); oxygen;Indichloromethane;at 0 ℃; for 6h; pH=11; aq. buffer;
    With potassium peroxomonosulfate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; methyl 2-N-acetylamido-4,6-O-benzylidene-2-deoxy-3-ulose-α-D-ribo-hexapyranoside;Indiethylene glycol dimethyl ether; water; acetonitrile;at 20 ℃; for 2.5h; pH=10.6; optical yield given as %ee; aq. buffer;
    With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III);optical yield given as %ee; enantioselective reaction; Inert atmosphere;
    With 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -78 ℃; optical yield given as %ee; enantioselective reaction;
    With Oxone; (1S,2R,5R)-ethyl 2',3-dioxo-8H-spiro[8-azabicyclo[3.2.1]octane-2,4'-[1,3]dioxolane]-8-carboxylate; sodium hydrogencarbonate;Inwater; acetonitrile;for 1.5h; optical yield given as %ee; enantioselective reaction;
    With Oxone; (1R,2R,5S)-ethyl 3'-methyl-2',3-dioxo-8H-spiro[8-azabicyco[3.2.1]octane-2,5'[1,3]oxazolidine]-8-carboxylate; sodium hydrogencarbonate;Inwater; acetonitrile;for 12.5h; optical yield given as %ee; enantioselective reaction;
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide;Indichloromethane;at 10 ℃; for 24h;
    With peracetic acid; (S,S)-Mn(N,N′-bis(2-pyridylmethyl)-2,2′-bipyrrolidine);Inacetonitrile;at 0 ℃; for 6h; optical yield given as %ee; enantioselective reaction;
    With sodium periodate;Intetrahydrofuran; dichloromethane; water;at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction;
    With pyridine N-oxide; sodium hypochlorite; disodium hydrogenphosphate; 5,5-methylenedi-[(R,R)-{N-(3-tertbutylsalicylidine)-N'-(3'-tert-butyl-5'-(N,N-dibutylmethylene)salicyladhyde)}-1,2-cyclohexanediaminato(2-)manganese(III)chloride];Indichloromethane; water;at 0 ℃; for 2.5h; pH=11.3; optical yield given as %ee; enantioselective reaction;
    With ethylenediaminetetraacetic acid; Agrocybe aegerita aromatic peroxygenase; oxygen; Flavin mononucleotide; at 20 ℃; pH=7; optical yield given as %ee; enantiospecific reaction; aq. phosphate buffer; Irradiation; Enzymatic reaction;
    With 3C25H43NO2*H3O24PW4; dihydrogen peroxide;Inchloroform-d1; water;at 50 ℃; for 48h; optical yield given as %ee; enantioselective reaction;
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -20 ℃; for 6h;
    With pyridine N-oxide; sodium hypochlorite;Indichloromethane;at 0 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction;
    With Agrocybe aegerita peroxygenase; dihydrogen peroxide;Inwater; acetonitrile;for 0.166667h; pH=7; enantioselective reaction; potassium phosphate buffer; Enzymatic reaction;
    With C24H32F3N3O4; dihydrogen peroxide;Intert-Amyl alcohol; acetonitrile;at 0 ℃; for 6h; optical yield given as %ee; enantioselective reaction; aq. buffer;
    With sodium hypochlorite; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 1-butyl-3-methylimidazolium Tetrafluoroborate;Inwater;at 0 ℃; for 2h; optical yield given as %ee; enantioselective reaction;
    isopropenylbenzene;With Mn(1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)(triflate)2; acetic acid;Inacetonitrile;for 0.0833333h; Inert atmosphere;
    With dihydrogen peroxide;Inacetonitrile;at -20 - 20 ℃; for 2h; enantioselective reaction; Inert atmosphere;
    With sodium hypochlorite; disodium hydrogenphosphate; ammonium acetate; at 0 ℃; pH=11.3; enantioselective reaction; Ionic liquid;
    With sodium hypochlorite;Indichloromethane;at 0 ℃; for 24h; pH=11.5; Reagent/catalyst; enantioselective reaction;
    79.5 % ee
    With 4-methylpyridine-1-oxide; sodium hypochlorite; C30H40ClMnN2O4;Indichloromethane;for 2h; Reagent/catalyst; enantioselective reaction;
    42.3 % ee
    With sodium hypochlorite; C10H13NO;Indichloromethane; water;at 0 ℃; for 24h; pH=11.3; Overall yield = 58.7 %Chromat.; enantioselective reaction;
    89 % ee
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide; nonane; C52H75MnN7O2;Indichloromethane; water;at 25 ℃; for 24h; Optical yield = 91.6 %ee;
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide; C54H42ClMnN2O6;Indichloromethane;at 0 ℃; Reagent/catalyst; Temperature; Overall yield = 92 %; enantioselective reaction;
    62 % ee
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide; C96H132Mn2N8O4;Indichloromethane; water;at 20 ℃; for 6h; pH=11.3; Reagent/catalyst; Temperature; Time; enantioselective reaction; Catalytic behavior;
    89 % ee
    With sodium hypochlorite; C48H64ClMnN2O4;Inaq. phosphate buffer;at 15 ℃; for 6h; pH=11.3; Reagent/catalyst; Overall yield = 90 %; Optical yield = 87 %ee; enantioselective reaction; Ionic liquid;
    With sodium hypochlorite; disodium hydrogenphosphate; C28H34ClMnN2O8S2(2-)*56H2O*40Zn(2+)*64HO(1-)*14NO3(1-); ammonium acetate;Indichloromethane;at 0 ℃; for 6h; Reagent/catalyst; Catalytic behavior; Cooling with ice;
    68 % ee
    With iodosylbenzene; C28H34ClMnN2O8S2(2-)*2Na(1+)*H2O; ammonium acetate;Indichloromethane;at 0 ℃; for 6h; Catalytic behavior;
    55 % ee
    With C52H76MnN7O2; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -40 ℃; for 5h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    89.6 % ee
    With pyridine N-oxide; C194H268Mn4N18O16; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at 0 ℃; for 1h; Overall yield = 66 %; enantioselective reaction; Catalytic behavior;
    74 % ee
    With D-glucose;Inaq. phosphate buffer; ethanol;at 30 ℃; for 5h; pH=8; Reagent/catalyst; enantioselective reaction; Enzymatic reaction;
    58.1 % ee
    With 2-Ethylhexanoic acid; C26H36F6MnN6O6S2; dihydrogen peroxide;Inwater; acetonitrile;at -30 ℃; for 1h; Overall yield = 88 %Chromat.; Optical yield = 26 %ee; enantioselective reaction;
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; at 25 ℃; for 4h; Temperature; Overall yield = 95 %Chromat.; Optical yield = 84.6 %ee; enantioselective reaction; Catalytic behavior;
    With 3-chloro-benzenecarboperoxoic acid;Intoluene;at -0.16 ℃; for 6h; Reagent/catalyst;
    78 % ee
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -20 ℃; Reagent/catalyst; Optical yield = 87.6 %ee; Catalytic behavior;
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -20 ℃; for 6h; Reagent/catalyst; Optical yield = 87.6 %ee;
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at -20 ℃; for 6h; Optical yield = 18 %ee; enantioselective reaction; Catalytic behavior;
    With sodium hypochlorite; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III);Indichloromethane;at 0 ℃; for 1h; Reagent/catalyst; Overall yield = 75 %; Catalytic behavior;
    43 % ee
    With pyridine N-oxide; sodium hypochlorite;Indichloromethane;at 0 ℃; for 1h; pH=11.5; Reagent/catalyst; Overall yield = 91 %; enantioselective reaction; Catalytic behavior;
    41 % ee
    With tert.-butylhydroperoxide; 4-methylmorpholine N-oxide;Indichloromethane;at 0 ℃; for 6h; Reagent/catalyst; Temperature; Solvent; Overall yield = 98 %Chromat.; Optical yield = 80 %ee; Catalytic behavior;
    With pyridine N-oxide; sodium chlorite; [(R,R)-(N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato)]manganese(III) chloride;Indichloromethane; water;at 0 ℃; for 1h; pH=11.5; Reagent/catalyst; Overall yield = 72 %; enantioselective reaction; Catalytic behavior;
    45 % ee
    With pyridine N-oxide; sodium hypochlorite;Inwater;at 2 ℃; for 0.5h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    75 % ee
    With tert.-butylhydroperoxide; 5Ni(2+)*1.4C3H7NO*9H2O*2C48H28N4O8(2-);Inacetonitrile;at 80 ℃; Overall yield = 66 %; Optical yield = 85 %ee; regioselective reaction; Sealed tube;
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide;Indichloromethane;at 20 ℃; for 24h; pH=11.5; Reagent/catalyst; Temperature; enantioselective reaction; Catalytic behavior;
    88 % ee
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide;Indichloromethane;at 20 ℃; for 24h; pH=11.5; Reagent/catalyst; Optical yield = 88 %ee; enantioselective reaction; Catalytic behavior;
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III);Indichloromethane;for 2h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    65 % ee
    With tert.-butylhydroperoxide; P450 peroxygenase T213M mutant;Inaq. phosphate buffer;at 35 ℃; for 0.166667h; pH=7.5; Reagent/catalyst; enantioselective reaction; Enzymatic reaction;
    63.2 % ee
    With 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at 0 ℃; enantioselective reaction;
    82 % ee
    With 1H-imidazole; sodium periodate; C49H71MnN4O2;Inwater; acetonitrile;for 5h; Catalytic behavior;
    82 % ee
    With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at 0 ℃; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    52 % ee
    With sodium periodate; C49H73MnN4O2;Indichloromethane;at -20 ℃; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    82 % ee
    With tert.-butylhydroperoxide; quadruple-mutant S148P/I161T/K199E/T214V Sulfolobus acidocaldarius CYP119 peroxygenase;Inaq. phosphate buffer;at 35 ℃; for 0.166667h; pH=7.5; Reagent/catalyst; enantioselective reaction; Enzymatic reaction;
    22.9 % ee
    With oxygen; isobutyraldehyde;Inacetonitrile;at 60 ℃; for 2h; under 750.075 Torr; enantioselective reaction;
    76 %Chromat.
    20 %Chromat.
    With C108H136Mn2N4O8; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at 0 ℃; for 1h; Reagent/catalyst; enantioselective reaction;
    79.5% ee
    With sodium hypochlorite; 4-Phenylpyridine 1-oxide;Indichloromethane; water;at 25 ℃; for 24h; pH=11.3; Reagent/catalyst; Catalytic behavior;
    89 % ee
    With iodosylbenzene; C44H36ClF18FeN2O2;Inacetonitrile;at 23 ℃; for 12h; Optical yield = 48 %ee; enantioselective reaction;
    With (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid;Innonane; dichloromethane;for 1h; Reagent/catalyst; Catalytic behavior;
    54 % ee
    With tert.-butylhydroperoxide;Inwater; 1,2-dichloro-ethane;at 80 ℃; for 4h; enantioselective reaction; Catalytic behavior;
    83 % ee
    With (S)-N-((R)-3,3-dimethylbutan-2-yl)-3,3-dimethyl-2-(((1-methyl-1H-imidazol-2-yl)methyl)amino)butanamide; iron(III) chloride hexahydrate; dihydrogen peroxide;Intert-Amyl alcohol; water;at 20 ℃; for 1h; Overall yield = 22 percentSpectr.; enantioselective reaction;
    16 % ee
    With 3C8H4O4(2-)*O(2-)*3Cr(3+)*C4H5O6(1-); oxygen; isobutyraldehyde;Inacetonitrile;at 80 ℃; for 8h; under 760.051 Torr; enantioselective reaction;
    85 % ee
    With iodosylbenzene; ammonium acetate;Indichloromethane;at -0.16 ℃; for 6h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    51 % ee
    With oxygen; isobutyraldehyde;Inethyl acetate;at 60 ℃; for 8h; under 750.075 Torr; enantioselective reaction;
    89 % ee
    With 1-Benzyl-1,4-dihydronicotinamide; styrene monooxygenase from Sphingopyxis fribergensis Kp5.2; flavin adenine dinucleotide; catalase from bovine liver;Indimethyl sulfoxide;at 30 ℃; for 1h; pH=7; enantioselective reaction; Catalytic behavior; Enzymatic reaction;
    89 % ee
    With pyridine N-oxide; sodium hypochlorite;Indichloromethane;at 0 ℃; for 0.666667h; enantioselective reaction;
    39 % ee
    Conditions
    ConditionsYield
    With sodium hypochlorite; ammonium acetate;Indichloromethane;at 0 ℃; for 5.5h; pH=11.3; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer;
    90%
    With dihydrogen peroxide; potassium hydrogencarbonate; (-)-2-cyanoheptahelicene;Inmethanol;for 48h; Ambient temperature;
    84%
    With sodium hypochlorite; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate;Inwater;at 0 ℃; for 2h; optical yield given as %ee; enantioselective reaction;
    63%
    With ruthenium trichloride; Trimethylacetic acid;Indichloromethane;at 40 ℃; for 24h; pH=7; Reagent/catalyst; Solvent; Temperature; enantioselective reaction; Enzymatic reaction;
    24%
    With Echerichia coli JM 109(pTAB19);Inphosphate buffer; 2,2,4-trimethylpentane;at 30 ℃; pH=7; Microbiological reaction;
    With iodosylbenzene; C28H34ClMnN2O8S2(2-)*56H2O*40Zn(2+)*64HO(1-)*14NO3(1-); ammonium acetate;Indichloromethane;at 0 ℃; for 6h; Reagent/catalyst; Catalytic behavior;
    99 % ee
    With C108H136Mn2N4O8; 3-chloro-benzenecarboperoxoic acid;Indichloromethane;at 0 ℃; for 1h; Reagent/catalyst; enantioselective reaction;
    97.4 % ee
    With oxygen; isobutyraldehyde;Inacetonitrile;at 52 ℃; for 6h; enantioselective reaction;
    94 % ee
    With iodosylbenzene; ammonium acetate;Indichloromethane;at -0.16 ℃; for 6h; Reagent/catalyst; enantioselective reaction; Catalytic behavior;
    99 % ee
    Conditions
    ConditionsYield
    With dmap; triethylamine; p-toluenesulfonyl chloride;Indichloromethane;at 0 - 50 ℃; for 24h; Inert atmosphere;
    92%
    Multi-step reaction with 2 steps
    2: NaH / diethyl ether
    With sodium hydride;Indiethyl ether;1: Tosylation / 2: Cyclization;
    (R)-Styrene oxide
    20780-53-4

    (R)-Styrene oxide

    methyl iodide
    74-88-4

    methyl iodide

    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    (R)-Styrene oxide;With sec.-butyllithium;Intetrahydrofuran;at -98 ℃; Inert atmosphere;
    methyl iodide;Intetrahydrofuran;Inert atmosphere;
    79%
    (R)-Styrene oxide;With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium;Intetrahydrofuran;at -98 ℃; for 0.166667h;
    methyl iodide;Intetrahydrofuran;at -98 - 20 ℃; Further stages.;
    dimethylsulfoxonium methylide
    70775-39-2,5367-24-8

    dimethylsulfoxonium methylide

    acetophenone
    98-86-2

    acetophenone

    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With C60H36LaLi3O6; Triphenylphosphine oxide;Intetrahydrofuran;at 20 - 23 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Molecular sieve;
    2-methyl-2-phenyloxirane
    2085-88-3

    2-methyl-2-phenyloxirane

    dimethylsulfoxonium methylide
    70775-39-2,5367-24-8

    dimethylsulfoxonium methylide

    (2R)-2-methyl-2-phenyloxetane

    (2R)-2-methyl-2-phenyloxetane

    (2R)-2-methyl-2-phenyloxetane
    1146489-93-1

    (2R)-2-methyl-2-phenyloxetane

    (R)-2-methyl-2-phenyloxirane
    2085-88-3,2404-43-5,21019-52-3,100018-61-9

    (R)-2-methyl-2-phenyloxirane

    (2S)-2-methyl-2-phenyloxirane
    2404-43-5

    (2S)-2-methyl-2-phenyloxirane

    Conditions
    ConditionsYield
    With (S)-La-Li3-(binaphthoxide)3; tris(2,4,6-trimethoxyphenyl)phosphine oxide;Intetrahydrofuran; hexane;at 45 ℃; for 48h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

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