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Donor-Acceptor-Cyclopropanes in Organic Synthesis

Publications

  • D. Reich, D. S. Müller, L. Schefzig, R. Zimmer,* H.-U. Reißig*
    One-Pot Generation of C≡X Bonds from Methyl 2-Siloxycyclopropanecarboxylates: Simple Syntheses of Functionalized Nitriles and Alkynes
    Synlett 2014, 25, 2265 – 2270.

  • T. H. Ngo, H. Berndt, D. Lentz, H.-U. Reißig*
    Linear and Cyclic Amides with a Thiophene Backbone: Ultrasound-Promoted Synthesis and Crystal Structures
    J. Org. Chem. 2012, 77, 9676 – 9683.

  • D. Gladow, H.-U. Reißig*
    Synthesis of Perfluoroalkyl-Substituted γ-Lactones and 4,5-Dihydropyridazin-3(2H)-ones via Donor-Acceptor Cyclopropanes
    Helv. Chim. Acta 2012, 95, 1818 1830.

  • H. Özbek, I. S. Veljkovic, H.-U. Reißig*
    Gewald Synthesis of Aminothiophene Carboxylic Acids Providing New Dipeptide Analogues
    Synlett 2008, 3145 – 3148.

  • H.-U. Reißig*, G. Böttcher, R. Zimmer
    New 1,3-Dihydroazepin-2-one Derivatives by [3,3]-Sigmatropic Rearrangement of Suitably Substituted 2-Alkenylcyclopropyl Isocyanates
    Can. J. Chem 2004, 82, 166 – 176.

  • H.-U. Reißig*, R. Zimmer
    Donor-Acceptor-Substituted Cyclopropane Derivatives and their Application in Organic Synthesis
    Chem. Rev. 2003, 103, 1151 – 1196.

  • P. K. Patra, H.-U. Reißig*
    Functionalized Azamacrocycles and Large-Ring α-Amino Esters by One-Pot Syntheses from Methyl 2-Siloxy-2-vinylcyclopropanecarboxylates
    Eur. J. Org. Chem. 2001, 4195 – 4206.

  • R. Zimmer, A. Ziemer, M. Gruner, I. Brüdgam, H. Hartl, H.-U. Reißig*
    Siloxycyclopropanes in Ugi Four-Component Reaction: A New Method for Synthesis of Highly Substituted Pyrrolidinone Derivatives
    Synthesis 2001, 1649 – 1658.

  • P. K. Patra, H..U. Reißig*
    An Efficient One-pot Synthesis of Functionalized Azamacrocycles from Methyl 2-Siloxy-2-vinylcyclopropanecarboxylates
    Synlett 2001, 33 – 36.

  • F. A. Khan, R. Czerwonka, H.-U. Reißig*
    Pd-Catalyzed Reactions of Donor-Acceptor Substituted Cyclopropanes and their Ring-opened Derivatives: Attempted Heck Cyclization and Novel One-pot Enolate Arylations
    Eur. J. Org. Chem. 2000, 3607 - 3617.

  • G. Böttcher, H.-U. Reißig*
    Synthesis of New Highly Substituted 1,3-Dihydroazepin-2-ones Starting from 2-Siloxycyclopropanecarboxylates
    Synlett 2000, 725 - 727.

  • 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.

  • A. Ullmann, M. Gruner, H.-U. Reißig*
    Synthesis of Functionalized Cyclophanes by Ring-Opening/Ring-Closure Cascade Reactions of Siloxycyclopropanes
    Chem. Eur. J. 1999, 5, 187 – 197.

  • A. Ullmann, H.-U. Reißig*, O. Rademacher
    A Repetitive Approach to the Synthesis of Medium and Large Ring Compounds with a Ring-Opening/Ring-Closure Cascade Reaction of Siloxycyclopropane Derivatives as Crucial Step
    Eur. J. Org. Chem. 1998, 2541 – 2549.

  • D. Sperling, H.-U. Reißig, J. Fabian*
    A DFT Study on the Vinylcyclopropanecarbaldehyde to 2,5-Dihydrooxepin Hetero-Cope-type Rearrangement and on Related Reactions
    Liebigs Ann./Recueil 1997, 2443 - 2450.

  • H.-U. Reißig*, R. Schumacher, D. Ferse
    Baeyer-Villiger Oxidations of γ-Oxo Esters - Determination of the Absolute Configurations of Methyl 2-Siloxycyclopropanecarboxylates - Interpretation of the Enantioselective Cyclopropanations of Silyl Enol Ethers
    Liebigs Ann./Recueil 1997, 2119 - 2124.

  • D. Sperling, H.-U. Reißig, J. Fabian*
    Quantenchemische Berechnungen zur chemischen Reaktivität: Isomerisierung einiger substituierter Cyclopropane
    Wiss. Z. Techn. Univ. Dresden 1997, 46, (Heft 5) 33 - 38.

  • R. Schumacher, F. Dammast, H.-U. Reißig*
    Screening of Various Catalysts for the Asymmetric Cyclopropanation of Structurally Typical Silyl Enol Ethers - Scope and Limitations of Evans's Bisoxazoline Copper Catalyst
    Chem. Eur. J. 1997, 3, 614 - 619.

  • R. Schumacher, H.-U. Reißig*
    Influence of Nucleophilicity of Silyl Enol Ethers on Stereoselectivities in Asymmetric Cyclopropanation Reactions
    Liebigs Ann./Recueil 1997, 521 - 526.

  • R. Schumacher, H.-U. Reißig*
    Stereoselective Cyclopropanation of Chiral Carbohydrate-Derived Enol Ethers
    Synlett 1996, 1121 - 1122.

  • M. Buchert, H.-U. Reißig*
    Rearrangement of Donor-Acceptor-Substituted Vinylcyclopropanes to Functionalized Cyclopentene Derivatives: Evidence for Zwitterionic Intermediates
    Liebigs Ann. 1996, 2007 - 2013.

  • F. A. Khan, R. Czerwonka, H.-U. Reißig*
    A Novel Pd(0)-Catalyzed One-Pot Transformation of Substituted Siloxycyclopropanes to Indane Derivatives
    Synlett 1996, 533 - 535.

  • J. Schnaubelt, E. Marks, H.-U. Reißig*
    [4+1] Cycloadditions of the Rhodium Di(methoxycarbonyl) Carbenoid to 2-Siloxy-1,3-dienes
    Chem. Ber. 1996, 129, 73 - 75.

  • J. Schnaubelt, A. Ullmann, H.-U. Reißig*
    An Efficient One-Pot Synthesis of Functionalized Cyclodecenone Derivatives from Siloxycyclopropanes
    Synlett 1995, 1223 – 1225.

  • J. Schnaubelt, H.-U. Reißig*
    Chelate Controlled Intramolecular Diels-Alder Reaction as Key for Synthesis of a Dihydromevinolin Precursor
    Synlett 1995, 452 - 454.

  • B. Hofmann, H.-U. Reißig*
    Characteristic Reactions of 4-Siloxy-2,5-dihydrooxepines: Desilylation, [2+2] and [4+2] Cycloadditions
    Chem. Ber. 1994, 127, 2337 - 2339.

  • B. Hofmann, H.-U. Reißig*
    Swern Oxidation of Alkenyl-Substituted 2-(tert-Butyldimethylsiloxy)-1-
    (hydroxymethyl)-cyclopropanes: A Novel and Flexible Route to Functionalized 2,5-Dihydrooxepines

    Chem. Ber. 1994, 127, 2327 - 2335.

  • B. Hofmann, H.-U. Reißig*
    Synthesis of New Alkenyl-Substituted 2-(tert-Butyldimethylsiloxy)cyclopropane-
    carboxylates and their Diastereoselective Conversion into (Hydroxymethyl)-
    cyclopropanes

    Chem. Ber. 1994, 127, 2315 - 2325.

  • K. Paulini, H.-U. Reißig*
    Synthesis of Dipeptides Containing Novel Cyclopropyl- and Cyclopropenyl-Substituted β- und γ-Amino Acids
    Liebigs Ann. Chem. 1994, 549 – 554.

  • F. Dammast, H.-U. Reißig*
    Synthese optisch aktiver 2-Siloxycyclopropancarbonsäureester durch asymmetrische Katalyse II. Einfluß der Silylenoletherstruktur auf die enantioselektive Cyclopropanierung mit Diazoessigsäuremethylester
    Chem. Ber. 1993,126, 2727 - 2732.

  • F. Dammast, H.-U. Reißig*
    Synthese optisch aktiver 2-Siloxycyclopropancarbonsäureester durch asymmetrische Katalyse I. Katalysatoreinfluß auf die Cyclopropanierung von (Z)-1-Phenyl-1-(trimethylsiloxy)prop-1-en
    Chem. Ber. 1993, 126, 2449 - 2456.

  • J. Schnaubelt, R. Zschiesche, H.-U. Reißig*, H. J. Lindner, J. Richter
    Synthese von Östronderivaten aus Siloxycyclopropancarbonsäureestern
    Liebigs Ann. Chem. 1993, 61 - 70.

  • B. Hofmann, H.-U. Reißig*
    Synthesis of Functionalized 2,5-Dihydrooxepines by [3,3]-Sigmatropic Rearrangement of Cyclopropane Derivatives
    Synlett 1993, 27 - 29.

  • H.-U. Reißig*, I. Reichelt, T. Kunz
    Methoxycarbonylmethylation of Aldehydes Via Siloxycyclopropanes: Methyl 3,3-Dimethyl-4-oxobutanoate
    Org. Synth. 1992, 71, 189 - 199.

  • K. Paulini, H.-U. Reißig*
    Ein effektiver Weg zu GABA-analogen Aminosäuren: Cyclopropanierung von N-silylierten Allylaminen und Enaminen
    Liebigs Ann. Chem. 1991, 455 – 461.

  • H.-E. Radunz*, H.-U. Reißig, G. Schneider, A. Riethmüller
    Synthese enantiomerenreiner γ-Keto-δ-aminosäuren, zentrale Bausteine vieler Enzyminhibitoren
    Liebigs Ann. Chem. 1990, 705 - 707.

  • T. Kunz, A. Janowitz, H.-U. Reißig*
    Eine flexible Synthese von 4-Oxobutansäuremethylestern und deren Derivaten
    Synthesis 1990, 43 - 47.

  • Patent:
    H.-E. Radunz, H.-U. Reißig
    Verfahren zur enantioselektiven Herstellung von γ-Keto-δ-aminosäurederivaten,
    Deutsches Patentamt (P 3919898 vom 19.6.1989)

  • R. Zschiesche, H.-U. Reißig*
    Reductive Transformations of Polyfunctional Nitro Compounds: Synthesis of Methyl 7-Aminoalkanoates and Five-Membered Cyclic Nitrones - Inter- and Intramolecular 1,3-Dipolar Cycloadditions
    Liebigs Ann. Chem. 1989, 551 - 557.

  • H.-U. Reißig*, H. Holzinger, G. Glomsda
    A Titanoxycyclopropane as Intermediate in a Highly Stereoselective Homoaldol Type Addition - Syntheses of cis-Substituted Tetrahydrofuran Derivatives
    Tetrahedron-Symposium-in-Print on Strain-Assisted Synthesis (L. Ghosez, Ed.), Tetrahedron 1989, 45, 3139 - 3150.

  • T. Kunz, H.-U. Reißig*
    Enantioselective Synthesis of Siloxycyclopropanes and of γ-Oxocarboxylates by Asymmetric Catalysis
    Tetrahedron Lett. 1989, 30, 2079 - 2082.

  • H.-U. Reißig*, R. Zschiesche, A. Wienand, M. Buchert
    Synthesis with Donor-Acceptor-Substituted Vinylcyclopropanes
    in "Strain and Its Implications in Organic Chemistry" (A. de Meijere, S. Blechert, Eds.), S. 51 - 58, Kluwer Academic Publishers, Dordrecht 1989.

  • R. Zschiesche, T. Hafner, H.-U. Reißig*
    Conversion of Polyfunctional Nitroalkanes into Carbonyl Compounds - Synthesis of the Pheromone Chalcogran and of Key Building Blocks for the Macrolides Pyrenophorin and Vermiculine
    Liebigs Ann. Chem. 1988, 1169 - 1173.

  • R. Zschiesche, H.-U. Reißig*
    Efficient Syntheses of Polyfunctional Nitro Compounds Using 2-Alkenyl-Substituted Methyl 2-Siloxycyclopropanecarboxylates as Key Building Blocks
    Liebigs Ann. Chem. 1988, 1165 - 1168.

  • C. Brückner, H. Holzinger, H.-U. Reißig*
    Diastereoselective Syntheses of Highly Substituted Methyl Tetrahydrofuran-3-carboxylates by Reactions of γ-Lactols with Silylated Nucleophiles
    J. Org. Chem. 1988, 53, 2450 – 2456.

  • C. Brückner, H.-U. Reißig*
    Efficient and Flexible Syntheses of Paraconic Esters and Other Highly Substituted Furanone Derivatives from Methyl 2-Siloxycyclopropanecarboxylates
    J. Org. Chem. 1988, 53, 2440 - 2450.

  • C. Brückner, B. Suchland, H.-U. Reißig*
    Eine neue Synthese von Pyrrolderivaten
    Liebigs Ann. Chem. 1988, 471 - 473.

  • C. Brückner, H.-U. Reißig*
    Thiophenderivate aus 2-Siloxycyclopropancarbonsäureestern durch neuartige 1,3- und 1,2-sigmatrope Umlagerungen
    Liebigs Ann. Chem. 1988, 465 - 470.

  • H.-U. Reißig
    Donor-Acceptor-Substituted Cyclopropanes: Versatile Building Blocks in Organic Synthesis
    Top. Curr. Chem. 1988, 144, 73 - 135.

  • R. Zschiesche, H.-U. Reißig*
    An Efficient Synthesis of 5-Membered Cyclic Nitrones from γ-Nitro Ketones
    Tetrahedron Lett. 1988, 29, 1685 - 1686.

  • R. Zschiesche, H.-U. Reißig*
    Eine Synthese von rac-Norbisabolid
    Liebigs Ann. Chem. 1987, 387 - 388.

  • C. Brückner, H.-U. Reißig*
    Geschwindigkeit und Regioselektivität der Hydrogenolyse einiger phenylsubstituierter Cyclopropane
    Chem. Ber. 1987, 120, 627 - 629.

  • C. Brückner, H.-U. Reißig*
    Katalytische Hydrogenolyse von 2-Siloxycyclopropancarbonsäureestern: Untersuchungen zu Chemo-, Regio- und Stereoselektivität
    Chem. Ber. 1987, 120, 617 - 626.

  • W. Bretsch, H.-U. Reißig*
    Synthese von β,γ-ungesättigten Ketonen und γ-Hydroxycarbonylverbindungen aus 2-Siloxycyclopropancarbonsäuremethylestern
    Liebigs Ann. Chem. 1987, 175 - 178.

  • R. Zschiesche, E. L. Grimm, H.-U. Reißig*
    Intramolekulare Diels-Alder-Reaktionen mit 2-Trimethylsiloxy-2-vinylcyclopropancarbonsäureestern als Schlüsselbausteinen
    Angew. Chem. 1986, 98, 1104 - 1105; Angew. Chem. Int. Ed. Engl. 1986, 25, 1086 - 1087.

  • H.-U. Reißig*, I. Reichelt, H. Lorey
    C-C-Verknüpfung durch Lewis-Säure-induzierte Cyclopropanringspaltung - Neue Wege zu hochsubstituierten Furan(on)derivaten
    Liebigs Ann. Chem. 1986, 1924 - 1939.

  • H.-U. Reißig*, H. Lorey
    Selenylierung, Sulfenylierung und Aminomethylierung von 2-Siloxycyclopropancarbonsäureestern durch Lewis-Säure-induzierte Ringöffnung
    Liebigs Ann. Chem. 1986, 1914 - 1923.

  • C. Brückner, H. Lorey, H.-U. Reißig*
    Diastereoselektive Synthese funktionalisierter Tetrahydrofuran-Derivate aus γ-Lactolen
    Angew. Chem. 1986, 98, 559 – 560.

  • C. Brückner, H. Lorey, H.-U. Reißig*
    Diastereoselektive Synthesis of Funktionalized Tetrahydrofuran Derivates from γ-Lactols
    Angew. Chem. Int. Ed. Engl. 1986, 25, 556 - 557.

  • H.-U. Reißig*, H. Lorey
    Lewis Acid promoted Additions of Cyclopropanes to Iminium Salts: A New Possibility for α-Methylene-γ-butyrolactone Synthesis
    J. Chem. Soc., Chem. Commun. 1986, 269 - 271.

  • E. L. Grimm, R. Zschiesche, H.-U. Reißig*
    2-Alkenyl-Substituted Methyl 2-Siloxycyclopropanecarboxylates as Masked Vinyl Ketones: Efficient Syntheses of Highly Functionalized Michael Adducts
    J. Org. Chem. 1985, 50, 5543 - 5545.

  • C. Brückner, H.-U. Reißig*
    Synthesis of Functionalized Furan Derivatives by Hydroxyalkylation of Methyl 2-Siloxycyclopropanecarboxylates
    J. Chem. Soc., Chem. Commun. 1985, 1512 - 1513.

  • H.-U. Reißig
    A Novel Rearrangement Leading to Methoxycarbonylmethylated Silyl Enol Ethers
    Tetrahedron Lett. 1985, 26, 3943 - 3946.

  • C. Brückner, H.-U. Reißig*
    Thiophenderivate durch neue Umlagerungen siloxysubstituierter Cyclopropancarbonsäureester
    Angew. Chem. 1985, 97, 578 - 579.

  • C. Brückner, H.-U. Reißig*
    Thiophene Derivatives by Novel Rearrangements of Siloxy-substituted Cyclopropanecarboxylates
    Angew. Chem. Int. Ed. Engl. 1985, 24, 588 - 589.

  • I. Reichelt, H.-U. Reißig*
    Neue Chrysanthemumsäurederivative durch Deprotonierung-Alkylierung
    Liebigs. Ann. Chem. 1985, 650 - 652.

  • E. L. Grimm, H.-U. Reißig*
    2-Siloxy-Substituted Methyl Cyclopropanecarboxylates as Building Blocks in Synthesis: Efficient One-Pot Conversion to γ-Butyrolactones
    J. Org. Chem. 1985, 50, 242 - 244.

  • H.-U. Reißig*, I. Reichelt
    Ring Cleaving Selenenylation and Sulfenylation of Cyclopropane Derivatives Promoted by TiCl4
    Tetrahedron Lett. 1984, 25, 5879 - 5880.

  • I. Reichelt, H.-U. Reißig*
    Eine einfache und flexible Synthese für 4,5-Dihydro-2H-3-pyridazinone
    Synthesis 1984, 786 - 787.

  • I. Reichelt, H.-U. Reißig*
    Zur Ringöffnung von 2-(Trimethylsilylmethyl)cyclopropancarbonsäuremethylester
    Liebigs Ann. Chem. 1984, 828 - 830.

  • I. Reichelt, H.-U. Reißig*
    Flexible und effektive Synthese für 4-Oxo-2-alkensäuremethylester
    Liebigs Ann. Chem. 1984, 820 - 827.

  • E. Kunkel, I. Reichelt, H.-U. Reißig*
    Ringöffnungsreaktionen von 2-Siloxycyclopropancarbonsäuremethylestern zu 4-Oxoalkansäurederivaten
    Liebigs Ann. Chem. 1984, 802 - 819.

  • I. Reichelt, H.-U. Reißig*
    Deprotonierung und diastereoselektive Alkylierung von 2-siloxysubstituierten Cyclopropancarbonsäuremethylestern
    Liebigs Ann. Chem. 1984, 531 - 551.

  • E. Kunkel, I. Reichelt, H.-U. Reißig*
    Synthese von 2-siloxysubstituierten Cyclopropancarbonsäuremethylestern
    Liebigs Ann. Chem. 1984, 512 - 530.

  • I. Reichelt, H.-U. Reißig
    Deprotonierung und diastereoselektive Alkylierung von Cyclopropancarbonsäuremethylestern
    Chem. Ber. 1983, 116, 3895 - 3914.

  • H.-U. Reißig*, I. Böhm
    Low Temperature Equilibration of Cyclopropanes by Lewis Acid Catalysis
    Tetrahedron Lett. 1983, 24, 715 - 718.

  • I. Böhm, R. Schulz, H.-U. Reißig*
    An Efficient and Highly Flexible Synthesis of α,β-Unsaturated γ-Oxoesters
    Tetrahedron Lett. 1982, 23, 2013 - 2016.

  • H.-U. Reißig*, I. Böhm
    High Diastereoselection in the Alkylation of Siloxy-Substituted Methyl Cyclopropanecarboxylates - Consequence of a Pyramidal Ester Enolate Anion?
    J. Am. Chem. Soc. 1982, 104, 1735 - 1737.

  • H.-U. Reißig
    Lewis-Acid-Promoted Additions of Carbonyl Compounds to Donor-Acceptor Substituted Cyclopropanes: A New Synthesis of 2,3-Dihydrofuran Derivatives
    Tetrahedron Lett. 1981, 22, 2981 - 2984.

  • I. Böhm, E. Hirsch, H.-U. Reißig*
    Alkylierung von Donor-Acceptor-substituierten Cyclopropanen: ein flexibler Weg zu 4-Oxocarbonsäureestern
    Angew. Chem. 1981, 93, 593 - 594.

  • I. Böhm, E. Hirsch, H.-U. Reißig*
    Alkylation of Donor-Acceptor Substituted Cyclopropanes: A Flexible Route to 4-Oxocarboxylic Acid Esters
    Angew. Chem. Int. Ed. Engl. 1981, 20, 574.

  • H.-U. Reißig*, E. Hirsch
    Donor-acceptor-substituierte Cyclopropane: Synthese und Ringöffnung zu 1,4-Di-carbonylverbindungen
    Angew. Chem. 1980, 92, 839 - 840.

  • H.-U. Reißig*, E. Hirsch
    Donor-Acceptor-Substituted Cyclopropanes: Synthesis und Ring Opening to 1,4-Dicarbonyl Compounds
    Angew. Chem. Int. Ed. Engl. 1980, 19, 813 - 814.