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Dominik Scherer - One of the best experts on this subject based on the ideXlab platform.
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2r 8ar 8 8 dimethoxycamphoryl sulfonyl Oxaziridine and 2r 8ar 8 8 dichlorocamphoryl sulfonyl Oxaziridine
Organic Syntheses, 2003Co-Authors: B C Chen, Christopher K Murphy, Anil Kumar, Thimma R Reddy, Charles Clark, Ping Zhou, Bryan M Lewis, Dinesh Gala, Ingrid Mergelsberg, Dominik SchererAbstract:(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)-(3-oxocamphorylsulfonyl)imine intermediate: (+)-(7,7-dimethoxy camphorylsulfonyl)imine intermediate: (+)-(7,7-dichlorocamphorylsulfonyl)imine product: (+)-(2R,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine (1) product: (−)-(2S,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine product: (+)-(2R,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl] Oxaziridine (2) product: (−)-(2S,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl]Oxaziridine Keywords: acetal (and thioacetal) formation; annulation, heterocyclic-[3]; annulation, heterocyclic-[3]; halogenation, chlorination; metalation reactions, lithium; oxidation, CH2 CO; oxidation, CN Oxaziridine; oxidation, CN Oxaziridine; selenium compounds, toxicity
Tehshik P Yoon - One of the best experts on this subject based on the ideXlab platform.
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Iron-catalyzed kinetic resolution of N-sulfonyl Oxaziridines
Chemical Science, 2014Co-Authors: Kevin S Williamson, James W. Sawicki, Tehshik P YoonAbstract:We have developed a highly selective kinetic resolution of N-sulfonyl Oxaziridines. This reaction utilizes an inexpensive and easily synthesized iron bis(oxazoline) catalyst to promote the efficient rearrangement of Oxaziridines to the corresponding N-sulfonyl imides; no sacrificial reagents are required to effect this resolution. This process is readily translated to gram scale, which provides a practical method for the preparation of structurally diverse, enantiopure N-sulfonyl Oxaziridines for use as reagents in organic synthesis.
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3 3 dimethyl 2 benzenesulfonyl Oxaziridine
e-EROS Encyclopedia of Reagents for Organic Synthesis, 2013Co-Authors: Kevin S Williamson, Tehshik P YoonAbstract:(3,3-Dimethyl-2-benzenesulfonyl Oxaziridine) [1261240-90-7] C9H11NO3S (MW: 213.25) InChI = 1S/C9H11NO3S/c1-9(2)10(13-9)14(11,12)8-6-4-3-5-7-8/h3-7H,1-2H3 InChIKey = QUFHTCYKCVJFKE-UHFFFAOYSA-N (3,3-Dimethyl-2-[(4-methylphenyl)sulfonyl]Oxaziridine) [118616-87-8] C10H13NO3S (MW: 227.28) InChI = 1S/C10H13NO3S/c1-8-4-6-9(7-5-8)15(12,13)11-10(2,3)14-11/h4-7H,1-3H3 InChIKey = ZHYXDWDENHARLM-UHFFFAOYSA-N (3,3-Dimethyl-2-[(4-nitrophenyl)sulfonyl]Oxaziridine) [1162661-83-7] C9H10N2O5S (MW: 258.25) InChI = 1S/C9H10N2O5S/c1-9(2)11(16-9)17(14,15)8-5-3-7(4-6-8)10(12)13/h3-6H,1-2H3 InChIKey = MGALDMWDZLAMCG-UHFFFAOYSA-N [3-(1,1-Dimethylethyl)-3-methyl-2-(phenylsulfonyl)Oxaziridine] (±)-[199001-53-1] C12H17NO3S (MW: 255.33) (S)-[1016243-76-7] (R)-[929877-50-9] InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3 InChIKey = WLAAJVMPTICBJF-UHFFFAOYSA-N InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3/t12-,13?/m0/s1 InChIKey = WLAAJVMPTICBJF-UEWDXFNNSA-N InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3/t12-,13?/m1/s1 InChIKey = WLAAJVMPTICBJF-PZORYLMUSA-N Analysis of Reagent Purity: 1H NMR. Handling, Storage, and Precaution: stable for extended periods when stored in refrigerator; prolonged heating leads to decomposition. Preparative Methods: compound 1a can be prepared in a two-step sequence. Reaction of acetone oxime, benzenesulfinyl chloride, and triethylamine generates an O-sulfinyl oxime that spontaneously rearranges to the corresponding N-sulfonyl imine. Oxidation of this intermediate with 3-chloroperoxybenzoic acid or potassium monoperoxysulfate yields Oxaziridine 1a. The analogous toluenesulfonyl Oxaziridines and 4-nitrobenzenesulfonyl Oxaziridines 1b and 1c have also been prepared by utilizing similar protocols.1–3 The related Oxaziridine 2 can be accessed in a two-step sequence from pinacolone. Heating equimolar amounts of pinacolone, benzenesulfonamide, and titanium tetrachloride affords the corresponding N-sulfonyl imine, which can be oxidized with 3-chloroperoxybenzoic acid4 or 3-chloroperoxybenzoic acid/KF5 to yield Oxaziridine 2. Purification: flash column chromatography and recrystallization. Related Reagents: 2-(benzenesulfonyl)-3-phenylOxaziridine (Davis' Oxaziridine). Solubility: soluble in CH2Cl2, CHCl3, THF, acetone, acetonitrile, and ethyl acetate; insoluble in hexane, pentane, and water.
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e-EROS Encyclopedia of Reagents for Organic Synthesis - 3,3‐Dimethyl‐2‐benzenesulfonyl Oxaziridine
Encyclopedia of Reagents for Organic Synthesis, 2013Co-Authors: Kevin S Williamson, Tehshik P YoonAbstract:(3,3-Dimethyl-2-benzenesulfonyl Oxaziridine) [1261240-90-7] C9H11NO3S (MW: 213.25) InChI = 1S/C9H11NO3S/c1-9(2)10(13-9)14(11,12)8-6-4-3-5-7-8/h3-7H,1-2H3 InChIKey = QUFHTCYKCVJFKE-UHFFFAOYSA-N (3,3-Dimethyl-2-[(4-methylphenyl)sulfonyl]Oxaziridine) [118616-87-8] C10H13NO3S (MW: 227.28) InChI = 1S/C10H13NO3S/c1-8-4-6-9(7-5-8)15(12,13)11-10(2,3)14-11/h4-7H,1-3H3 InChIKey = ZHYXDWDENHARLM-UHFFFAOYSA-N (3,3-Dimethyl-2-[(4-nitrophenyl)sulfonyl]Oxaziridine) [1162661-83-7] C9H10N2O5S (MW: 258.25) InChI = 1S/C9H10N2O5S/c1-9(2)11(16-9)17(14,15)8-5-3-7(4-6-8)10(12)13/h3-6H,1-2H3 InChIKey = MGALDMWDZLAMCG-UHFFFAOYSA-N [3-(1,1-Dimethylethyl)-3-methyl-2-(phenylsulfonyl)Oxaziridine] (±)-[199001-53-1] C12H17NO3S (MW: 255.33) (S)-[1016243-76-7] (R)-[929877-50-9] InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3 InChIKey = WLAAJVMPTICBJF-UHFFFAOYSA-N InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3/t12-,13?/m0/s1 InChIKey = WLAAJVMPTICBJF-UEWDXFNNSA-N InChI = 1S/C12H17NO3S/c1-11(2,3)12(4)13(16-12)17(14,15)10-8-6-5-7-9-10/h5-9H,1-4H3/t12-,13?/m1/s1 InChIKey = WLAAJVMPTICBJF-PZORYLMUSA-N Analysis of Reagent Purity: 1H NMR. Handling, Storage, and Precaution: stable for extended periods when stored in refrigerator; prolonged heating leads to decomposition. Preparative Methods: compound 1a can be prepared in a two-step sequence. Reaction of acetone oxime, benzenesulfinyl chloride, and triethylamine generates an O-sulfinyl oxime that spontaneously rearranges to the corresponding N-sulfonyl imine. Oxidation of this intermediate with 3-chloroperoxybenzoic acid or potassium monoperoxysulfate yields Oxaziridine 1a. The analogous toluenesulfonyl Oxaziridines and 4-nitrobenzenesulfonyl Oxaziridines 1b and 1c have also been prepared by utilizing similar protocols.1–3 The related Oxaziridine 2 can be accessed in a two-step sequence from pinacolone. Heating equimolar amounts of pinacolone, benzenesulfonamide, and titanium tetrachloride affords the corresponding N-sulfonyl imine, which can be oxidized with 3-chloroperoxybenzoic acid4 or 3-chloroperoxybenzoic acid/KF5 to yield Oxaziridine 2. Purification: flash column chromatography and recrystallization. Related Reagents: 2-(benzenesulfonyl)-3-phenylOxaziridine (Davis' Oxaziridine). Solubility: soluble in CH2Cl2, CHCl3, THF, acetone, acetonitrile, and ethyl acetate; insoluble in hexane, pentane, and water.
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N-Nosyl Oxaziridines as terminal oxidants in copper(II)-catalyzed olefin oxyaminations
Tetrahedron Letters, 2010Co-Authors: Sandra M. Deporter, Kevin S Williamson, Ashley C. Jacobsen, Katherine M. Partridge, Tehshik P YoonAbstract:We report that N-4-nosyl-3-phenylOxaziridine is an effective terminal oxidant for copper(II)-catalyzed oxyamination recently developed in our labs. This Oxaziridine can be prepared on multi-gram scale and is easily purified by recrystallization. The products of oxyamination using this Oxaziridine bear protecting groups that can be readily removed in high yields under mild conditions.
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Oxaziridine-Mediated Intramolecular Amination of sp3-Hybridized C−H Bonds
Journal of the American Chemical Society, 2009Co-Authors: Charles P Allen, Tamas Benkovics, Amanda K Turek, Tehshik P YoonAbstract:We describe a new Oxaziridine-mediated approach to the amination of sp3-hybridized C−H bonds. In the presence of a copper(II) catalyst, N-sulfonyl Oxaziridines participate in efficient intramolecular cyclization reactions to afford a variety of piperidine and tetrahydroisoquinoline structures. The aminal intermediates provide a convenient functional handle for further elaboration of these structures, demonstrating the utility of this new methodology for the rapid construction of structurally complex nitrogen-containing heterocycles.
Anil Kumar - One of the best experts on this subject based on the ideXlab platform.
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2r 8ar 8 8 dimethoxycamphoryl sulfonyl Oxaziridine and 2r 8ar 8 8 dichlorocamphoryl sulfonyl Oxaziridine
Organic Syntheses, 2003Co-Authors: B C Chen, Christopher K Murphy, Anil Kumar, Thimma R Reddy, Charles Clark, Ping Zhou, Bryan M Lewis, Dinesh Gala, Ingrid Mergelsberg, Dominik SchererAbstract:(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)-(3-oxocamphorylsulfonyl)imine intermediate: (+)-(7,7-dimethoxy camphorylsulfonyl)imine intermediate: (+)-(7,7-dichlorocamphorylsulfonyl)imine product: (+)-(2R,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine (1) product: (−)-(2S,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine product: (+)-(2R,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl] Oxaziridine (2) product: (−)-(2S,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl]Oxaziridine Keywords: acetal (and thioacetal) formation; annulation, heterocyclic-[3]; annulation, heterocyclic-[3]; halogenation, chlorination; metalation reactions, lithium; oxidation, CH2 CO; oxidation, CN Oxaziridine; oxidation, CN Oxaziridine; selenium compounds, toxicity
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Organic Syntheses - (+)‐(2R,8aR*)‐[(8,8‐Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)‐(2R,8aR*)‐[(8,8‐Dichlorocamphoryl)Sulfonyl]Oxaziridine
Organic Syntheses, 2003Co-Authors: B.‐c. Chen, Christopher K Murphy, Anil Kumar, Charles Clark, Ping Zhou, Bryan M Lewis, Dinesh Gala, Ingrid Mergelsberg, R. Thimma Reddy, Dominik Hermann SchererAbstract:(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)-(3-oxocamphorylsulfonyl)imine intermediate: (+)-(7,7-dimethoxy camphorylsulfonyl)imine intermediate: (+)-(7,7-dichlorocamphorylsulfonyl)imine product: (+)-(2R,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine (1) product: (−)-(2S,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine product: (+)-(2R,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl] Oxaziridine (2) product: (−)-(2S,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl]Oxaziridine Keywords: acetal (and thioacetal) formation; annulation, heterocyclic-[3]; annulation, heterocyclic-[3]; halogenation, chlorination; metalation reactions, lithium; oxidation, CH2 CO; oxidation, CN Oxaziridine; oxidation, CN Oxaziridine; selenium compounds, toxicity
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2r 8as 10 camphorylsulfonyl Oxaziridine
Organic Syntheses, 2003Co-Authors: James C Towson, Michael C Weismiller, Anil Kumar, Aurelia C Sheppard, F A DavisAbstract:(+)-(2R,8aS)-10-(camphorylsulfonyl)Oxaziridine intermediate: (+)-(1S)-10-Camphorsulfonamide intermediate: (−)-(camphorsulfonyl)imine product: (+)-(2R, 8aS)-10-CamphorylsulfonylOxaziridine product: (−)-(2S,8aR)-10-(camphorylsulfonyl)Oxaziridine Keywords: annulation, heterocyclic-[3]; annulation, heterocyclic-[5]; oxidation, CN Oxaziridine; sulfonation, N-sulfonation; stirrers, teflon bearing
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Organic Syntheses - (+)‐(2R,8aS)‐10‐(Camphorylsulfonyl)Oxaziridine
Organic Syntheses, 2003Co-Authors: James C Towson, Michael C Weismiller, Anil Kumar, Aurelia C Sheppard, Franklin A DavisAbstract:(+)-(2R,8aS)-10-(camphorylsulfonyl)Oxaziridine intermediate: (+)-(1S)-10-Camphorsulfonamide intermediate: (−)-(camphorsulfonyl)imine product: (+)-(2R, 8aS)-10-CamphorylsulfonylOxaziridine product: (−)-(2S,8aR)-10-(camphorylsulfonyl)Oxaziridine Keywords: annulation, heterocyclic-[3]; annulation, heterocyclic-[5]; oxidation, CN Oxaziridine; sulfonation, N-sulfonation; stirrers, teflon bearing
Thimma R Reddy - One of the best experts on this subject based on the ideXlab platform.
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2r 8ar 8 8 dimethoxycamphoryl sulfonyl Oxaziridine and 2r 8ar 8 8 dichlorocamphoryl sulfonyl Oxaziridine
Organic Syntheses, 2003Co-Authors: B C Chen, Christopher K Murphy, Anil Kumar, Thimma R Reddy, Charles Clark, Ping Zhou, Bryan M Lewis, Dinesh Gala, Ingrid Mergelsberg, Dominik SchererAbstract:(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)-(3-oxocamphorylsulfonyl)imine intermediate: (+)-(7,7-dimethoxy camphorylsulfonyl)imine intermediate: (+)-(7,7-dichlorocamphorylsulfonyl)imine product: (+)-(2R,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine (1) product: (−)-(2S,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine product: (+)-(2R,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl] Oxaziridine (2) product: (−)-(2S,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl]Oxaziridine Keywords: acetal (and thioacetal) formation; annulation, heterocyclic-[3]; annulation, heterocyclic-[3]; halogenation, chlorination; metalation reactions, lithium; oxidation, CH2 CO; oxidation, CN Oxaziridine; oxidation, CN Oxaziridine; selenium compounds, toxicity
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chemistry of Oxaziridines 17 n phenylsulfonyl 3 3 dichlorocamphoryl Oxaziridine a highly efficient reagent for the asymmetric oxidation of sulfides to sulfoxides
Journal of the American Chemical Society, 1992Co-Authors: Franklin A Davis, Thimma R Reddy, Patrick J CarrollAbstract:The synthesis, structure, and enantioselective oxidations of a new chiral N-sulfonylOxaziridine 12c [3,3-dichloro- 1,7,7-trimethyl-2'-(phenylsulfonyl)spiro[bicyclo[2.2.1]heptane-2,3'-Oxaziridine]] are reported. This oxidant, which exhibits remarkably high and predictable ee's for the enantioselective oxidation of prochiral sulfides to sulfoxides, is prepared in three steps from (+)- or (-)-camphor in 50% overall yield
B C Chen - One of the best experts on this subject based on the ideXlab platform.
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2r 8ar 8 8 dimethoxycamphoryl sulfonyl Oxaziridine and 2r 8ar 8 8 dichlorocamphoryl sulfonyl Oxaziridine
Organic Syntheses, 2003Co-Authors: B C Chen, Christopher K Murphy, Anil Kumar, Thimma R Reddy, Charles Clark, Ping Zhou, Bryan M Lewis, Dinesh Gala, Ingrid Mergelsberg, Dominik SchererAbstract:(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)Sulfonyl]Oxaziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)Sulfonyl]Oxaziridine intermediate: (−)-(3-oxocamphorylsulfonyl)imine intermediate: (+)-(7,7-dimethoxy camphorylsulfonyl)imine intermediate: (+)-(7,7-dichlorocamphorylsulfonyl)imine product: (+)-(2R,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine (1) product: (−)-(2S,8aR*)-[(8,8-dimethoxycamphoryl)sulfonyl]Oxaziridine product: (+)-(2R,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl] Oxaziridine (2) product: (−)-(2S,8aR*)-[(8,8-dichlorocamphoryl)sulfonyl]Oxaziridine Keywords: acetal (and thioacetal) formation; annulation, heterocyclic-[3]; annulation, heterocyclic-[3]; halogenation, chlorination; metalation reactions, lithium; oxidation, CH2 CO; oxidation, CN Oxaziridine; oxidation, CN Oxaziridine; selenium compounds, toxicity
