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1,2-Oxazine Derivatives by Hetero Diels-Alder Reaction and Subsequent Transformations

Publications

  • H.-U. Reißig, R. Zimmer
    Nitrosoalkenes
    in Science of Synthesis (Knowledge Update) 2015/2, Thieme Verlag, Stuttgart, 315 – 334.

  • N. Moinizadeh, R. Klemme, M. Kansy, R. Zimmer,* H.-U. Reißig*
    Convenient Syntheses of Enantiopure 1,2-Oxazin-4-yl Nonaflates and Phosphates and Their Palladium-Catalyzed Cross-Couplings
    Synthesis 2013, 45, 2752 – 2762.

  • I. Linder, M. Gerhard, L. Schefzig, M. Andrä, C. Bentz, H.-U. Reißig,* R. Zimmer
    A Modular Synthesis of Functionalized Pyridines through Lewis-Acid-Mediated and Microwave-Assisted Cycloadditions between Azapyrylium Intermediates and Alkynes
    Eur. J. Org. Chem. 2011, 6070 – 6078.

  • R. Zimmer, M. Buchholz, M. Collas, J. Angermann, K. Homann, H.-U. Reißig*
    1,2-Oxazines as Building Blocks for Stereoselective Synthesis: Preparation of Oxygen-Substituted 1,2-Oxazines, either by Alcohol Addition or by Epoxidation, and Subsequent Hydrogenation Leading to 1,2-Amino Alcohols and Pyrrolidines
    Eur. J. Org. Chem. 2010, 4111 – 4122.

  • R. Zimmer, E. Schmidt, M. Andrä, M.-A. Duhs, I. Linder, H.-U. Reißig*
    Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
    Beilstein Journal of Organic Chemistry 2009, 5, No. 44.

  • R. Zimmer, M. Collas, R. Czerwonka, U. Hain, H.-U. Reißig*
    A New Access to Pyrrolizidine Derivatives: Ring Contraction of Methyl (E)-[1,2-Oxazin-3-yl]propenoates
    Synthesis 2008, 237 – 244.

  • H.-U. Reißig*, K. Homann, F. Hiller, R. Zimmer
    A Stereoselective Access to Dihydroxylated Pyrrolidines by Reductive Ring Contraction of 1,2-Oxazines.
    Synthesis, 2007, 2681 – 2689.

  • H.-U. Reißig, R. Zimmer*
    1-Nitrosoalkenes
    in: Science of Synthesis, 2006, Vol. 33, 371 – 389.

  • E. Schmidt, H.-U. Reißig*, R. Zimmer
    Regio- and Stereoselective 1,3-Dipolar Cycloadditions to 6H-1,2-Oxazines Leading to New Heterobicyclic Compounds
    Synthesis 2006, 2074 - 2084.

  • M. Buchholz, H.-U. Reißig*
    Enantioselective Syntheses of the Pyrrolidine Core of Endothelin Antagonist ABT-627 (Atrasentan) via 1,2-Oxazines
    Eur. J. Org. Chem. 2003, 3524 - 3533.

  • R. Zimmer, B. Orschel, S. Scherer, H.-U. Reißig*
    Hetero Diels-Alder Reactions of Nitroso Alkenes with Alkoxyallene Derivatives Bearing Carbohydrate Auxiliaries - Asymmetric Synthesis of 6H-1,2-Oxazines and Subsequent Reductive Transformations
    Synthesis 2002, 1553 - 1563.

  • M. Buchholz, F. Hiller, H.-U. Reißig*
    Synthesis of Enantioenriched 2-Substituted 4-Phenylbutylamines by Hydrogenolysis of Optically Pure 6-Alkoxy-5,6-dihydro-4H-1,2-oxazines
    Eur. J. Org. Chem. 2002, 2838 - 2843.

  • M. Buchholz, H.-U. Reißig*
    Highly Stereoselective and Flexible Synthesis of 6-Alkoxy-5,6-dihydro-4H-1,2-oxazines by Conjugate Addition of Organolithium Compounds to 6H-1,2-Oxazines Followed by Trapping with Electrophiles
    Synthesis 2002, 1412 - 1422.

  • A. A. Tishkov, H.-U. Reißig*, S. Ioffe
    Preparation of Cyclic and Bicyclic γ-Amino Acid Derivatives from Methyl 6-Ethoxy-5,6-dihydro-4H-1,2-oxazine-4-carboxylate
    Synlett 2002, 863 - 866.

  • H. Hartl*, I Brüdgam, H.-U. Reißig, M. Buchholz
    Crystal Structure of (4S*,5R*,6S*)-6-Ethoxy-4-(1R*)-(1-hydroxy-1-
    phenyl)methyl-3,5-diphenyl-5,6-dihydro-4H-1,2-oxazine, C25H25NO3
    Z. Kristallogr. NCS 2001, 216, 591 – 592.

  • E. Schmidt, H.-U. Reißig, O. Rademacher*
    Crystal structure of 3aS*,4S*,7aR*-4-ethoxy-3a,7a-dihydro-3,7-diphenyl-4H-1,5-
    dioxa-2,6-diaza-indene, C19H18N2O3

    Z. Kristallogr. NCS 2000, 215, 283 - 284.

  • R. Zimmer, K. Homann, J. Angermann, H.-U. Reißig*
    Stereoselective Preparation of 4,5-Dihydroxy-5,6-dihydro-4H-1,2-oxazines and Their Derivatives
    Synthesis 1999, 1223 - 1235.

  • D. Sperling, H.-U. Reißig, J. Fabian*
    1,3-Sigmatropic Rearrangements of Divinylcyclopropane Derivatives and Hetero Analogs in Competition with Cope-Type Rearrangements – A DFT Study
    Eur. J. Org. Chem. 1999, 1107 – 1114.

  • R. Zimmer, F. Hiller, H.-U. Reißig*
    1,4-Addition of Organolithium Compounds to 6-Ethoxy-3-phenyl-6H-1,2-oxazine
    Heterocycles 1999, 50, 393 - 401.

  • K. Homann, J. Angermann, M. Collas, R. Zimmer, H.-U. Reißig*
    Synthesis of 6-Ethoxy-6H-1,2-oxazines by Hetero Diels-Alder Reaction of 1-Bromo-2-ethoxyethene with α-Nitroso Alkenes
    J. Prakt. Chem. 1998, 340, 649 – 655.

  • U. Jänicke-Rößler, G. Zahn*, F. Hiller, H.-U. Reißig
    Crystal structure of (6S)-6-[(1R,2S,5R)-(–)-2-Ιsopropyl-5-methylcyclo-
    hexyloxy]-3-phenyl-6H-1,2-oxazine, [ONC(CH)3(C6H5)O(CH)2(CH2)2CHCH2CH(CH3)2CH3]

    Z. Kristallogr. 1998, 213, 261 - 262.

  • R. Zimmer, J. Angermann, U. Hain, F. Hiller, H.-U. Reißig*
    Hetero Diels-Alder Reactions of 2-Chloro-1-nitroso-1-phenylethene: Preparation of Novel 4-Chloro-Substituted 1,2-Oxazines and Subsequent Reactions
    Synthesis 1997, 1467 - 1474.

  • D. Sperling, A. Mehlhorn, H.-U. Reißig, J. Fabian*
    Theoretical Study of Pericyclic Reactions of Nitrosoethylene and (Thionitroso)ethylene
    Liebigs Ann. 1996, 1615 - 1621.

  • R. Zimmer, H.-U. Reißig*
    Lithiated 3-trifluoromethyl-substituted 1,2-Oxazines and their Reactions
    J. Fluorine Chem. 1996, 80, 21 - 26.

  • R. Zimmer, H.-U. Reißig*, K. Homann
    1,2-Azapyrylium Ions: Properties and Synthetic Applications
    J. Prakt. Chem. 1995, 337, 521 - 528.

  • J. Angermann, K. Homann, H.-U. Reißig*, R. Zimmer
    Synthesis and cis-Dihydroxylation of 6H-1,2-Oxazines - Synthesis of Dihydroxyprolinols
    Synlett 1995, 1014 - 1016.

  • K. Paulini, H.-U. Reißig*, P. Rademacher
    On the Reactivity of N,N-Bis(trimethyl)silylated Enamines: Model Studies on Hetero Diels-Alder Reactions and Other Cycloadditions
    J. Prakt. Chem. 1995, 337, 209 - 215.

  • K. Homann, R. Zimmer, H.-U. Reißig*
    Reactions of Azapyrylium Ions with Nucleophiles: From Crazy Products to a Novel Pyridine Synthesis
    Heterocycles 1995, 40, 531 - 537.

  • K. Paulini, A. Gerold, H.-U. Reißig*
    Reactions of 6-[Bis(trimethylsilyl)amino]-5,6-dihydro-4H-1,2-oxazines
    Liebigs Ann. 1995, 667 - 671.

  • T. Arnold, H.-U. Reißig, J. Richter, H. J. Lindner*, H. Paulus
    Crystal structure of 3-O-(5,6-dihydro-5-methyl-3-phenyl-4H-1,2-oxazin-6-yl)
    -1,2:5,6-di-O-isopropyliden-α-D-glucofuranose,
    O(CH)4OCO(CH3)2CHCH2OCO(CH3)2OCHCHCH2CNO(CH3)(C6H5)

    Z. Kristallogr. 1994, 209, 903 - 904.

  • K. Homann, H.-U. Reißig, S. Foro, H. J. Lindner*
    Crystal structure of 2-methyl-6-phenyl-pyridin-3-al, (C6H5)C(CH)2CCNCHO(CH3)
    Z. Kristallogr. 1994, 209, 902.

  • R. Zimmer, T. Arnold, K. Homann, H.-U. Reißig*
    An Efficient and Simple Synthesis of 3,4,5,6-Tetrahydro-2H-1,2-oxazines by Sodium Cyanoborohydride Reduction of 5,6-Dihydro-4H-1,2-oxazines
    Synthesis 1994, 1050 - 1056.

  • K. Paulini, H.-U. Reißig*
    Diastereoselective Radical Bromination of 5,6-Dihydro-4H-1,2-oxazines and Subsequent Substitution Reactions with Nitrogen Nucleophiles
    Chem. Ber. 1994, 127, 685 - 689.

  • R. Zimmer*, K. Homann, H.-U. Reißig*
    Reductive Transformations of 6H-1,2-Oxazines with Hydride Reagents: Formation of Aziridines and 3-Hydroxyalkylated 1,2-Oxazines
    Liebigs Ann. Chem. 1993, 1155 - 1157.

  • R. Zimmer, M. Hoffmann, H.-U. Reißig*
    Model Studies of the Reduction of 3-Phenyl-6H-1,2-oxazines, Chemo- and Stereoselectivity: Synthesis of Amino Alcohols, Amino Acids, and Related Compounds
    Chem. Ber. 1992, 125, 2243 - 2248.

  • T. Arnold, B. Orschel, H.-U. Reißig*
    Diacetonglucose als Hilfsgruppe bei der asymmetrischen Hetero-Diels-Alder-Reaktion mit Nitrosoalkenen
    Angew. Chem. 1992, 104, 1084 - 1086.

  • T. Arnold, B. Orschel, H.-U. Reißig*
    Diacetoneglucose as Auxiliary Group for the Asymmetric Hetero-Diels-Alder Reaction with Nitrosoalkenes
    Angew. Chem. Int. Ed. Engl. 1992, 31, 1033 - 1035.

  • R. Zimmer*, M. Collas, M. Roth, H.-U. Reißig
    6-Siloxy-Substituted 5,6-Dihydro-4H-1,2-oxazines as Key Building Blocks for Natural Products
    Liebigs Ann. Chem. 1992, 709 - 714.

  • R. Zimmer, H.-U. Reißig*, H.J. Lindner
    Unerwartete Bildung von β-Lactamen aus 6H-1,2-Oxazinen unter Lewis-Säure-Einwirkung
    Liebigs Ann. Chem. 1992, 621 - 624.

  • R. Zimmer, H.-U. Reißig*
    Efficient Synthesis of Trifluoromethyl-Substituted 5,6-Dihydro-4H-1,2-oxazines by the Hetero-Diels-Alder Reaction of 1,1,1-Trifluoro-2-nitroso-2-propene and Electron-Rich Olefins
    J. Org. Chem. 1992, 57, 339 - 347.

  • C. Unger, R. Zimmer, H.-U. Reißig*, E.-U. Würthwein
    Deprotonation of 5,6-Dihydro-5-methylene-4H-1,2-oxazines and Regioselective Reactions with Electrophiles
    Chem. Ber. 1991, 124, 2279 - 2287.

  • R. Zimmer, H.-U. Reißig*
    Synthesis of 6H-1,2-Oxazines by Hetero Diels-Alder Reactions of Nitroso Alkenes towards Methoxyallenes
    Liebigs Ann. Chem. 1991, 553 - 562.

  • H.-U. Reißig*, C. Hippeli
    Lithiated 5,6-Dihydro-4H-1,2-oxazines: Synthesis, Highly Diastereoselective Reactions with Electrophiles, and Subsequent Transformations
    Chem. Ber. 1991, 124, 115 - 127.

  • H.-U. Reißig*, C. Hippeli, T. Arnold
    On the Mechanism of Diels-Alder Reactions of Nitroso Alkenes: Exo/Endo-Selectivity, Stereospecificity, E/Z-Selectivity, and Relative Reactivity of Various Olefins
    Chem. Ber. 1990, 123, 2403 - 2411.

  • T. Arnold, H.-U. Reißig*
    Hetero Diels-Alder Reactions of Optically Active Enol Ethers with a Nitroso Alkene: Asymmetric Synthesis of 1,2-Oxazine Derivatives
    Synlett 1990, 514 - 516.

  • C. Hippeli, H.-U. Reißig*
    Reductive Transformations of 5,6-Dihydro-4H-1,2-oxazines: Synthesis of 4-Hydroxy Ketoximes, N-Hydroxypyrrolidine Derivatives, and Other Nitrogen Containing Compounds
    Liebigs Ann. Chem. 1990, 475 - 481.

  • C. Hippeli, R. Zimmer, H.-U. Reißig*
    Transition Metal and Acid-Induced Transformations of 6-Siloxy-Substituted
    5,6-Dihydro-4H-1,2-oxazines: Preparation of Pyrroles, Nitrones, 1,4-Dicarbonyl Compounds and Derivatives Thereof

    Liebigs Ann. Chem. 1990, 469 - 474.

  • C. Hippeli, H.-U. Reißig*
    Synthesis of Trialkylsiloxy-Substituted and Other 5,6-Dihydro-4H-1,2-oxazines by Hetero Diels-Alder Reactions of Nitroso Alkenes - Preparative Scope and Diastereoselectivity
    Liebigs Ann. Chem. 1990, 217 - 226.

  • C. Hippeli, N. Basso, F. Dammast, H.-U. Reißig*
    A Practical Method for the Separation of E/Z-Isomeric Silyl Enol Ethers by Kinetic Resolution
    Synthesis 1990, 26 – 27.

  • R. Zimmer, H.-U. Reißig*
    Nucleophile Substitution an 6H-1,2-Oxazinen über Azapyrylium-Ionen
    Synthesis 1989, 908 - 911.

  • R. Zimmer, H.-U. Reißig*
    Methoxyallene als Komponenten in Diels-Alder-Reaktionen mit inversem Elektronenbedarf: Synthese von 6H-1,2-Oxazinen
    Angew. Chem. 1988, 100, 1576 - 1577.

  • R. Zimmer, H.-U. Reißig*
    Methoxyallenes as Components in Diels-Alder Reactions with Inverse Electron Demand: Synthesis of 6H-1,2-Oxazines
    Angew. Chem. Int. Ed. Engl. 1988, 27, 1518 - 1519.

  • C. Hippeli, H.-U. Reißig*
    Highly Diastereoselective Deprotonation and Substitution of Chiral 5,6-Dihydro-4H-1,2-oxazines
    J. Org. Chem. 1988, 53, 3884 - 3886.

  • C. Hippeli, H.-U. Reißig*
    Efficient Synthesis of 6-Trimethylsiloxy- and 6-(Trimethylsilyl)methyl-3-phenyl-
    5,6-dihydro-4H-1,2-oxazines by Cycloaddition of α-Nitrosostyrene to Silyl Enol Ethers and Allyltrimethylsilane

    Synthesis 1987, 77 - 79.