Preparative organic and bioorganic chemistry

Preparative organic and bioorganic chemistry: Methods of selective halogenations, esp. fluorinations, selective syntheses of fluorinated analogues of natural products, enzymatic methods in organic synthesis, biotransformations with microorganisms, chemistry of aliphatic and alicyclic compounds (including terpenes), synthesis and reactions of medium-sized rings - transannular reactivity.

Drittmittelgeber:

Deutsche Forschungsgemeinschaft, Graduate College "Hochreaktive Mehrfach-bindungssysteme", Fonds der Chemischen Industrie, Volkswagen-Stiftung, EU INTAS, DAAD, Ministry of Education, Science, Sports and Cultute, Japan. Merck KGaA

Veröffentlichungen:

G. Haufe, G. Alvernhe, A. Laurent, T. Ernet, O. Goj, S. Kröger, A. Sattler: "Bromofluorination of Alkenes: 1-Bromo-2-fluoro-2-phenylpropane", Org. Synth. 1999, 76, 159-168.

S. Otten, R. Fröhlich, G. Haufe,: "Synthesis and Structural Characterization of Enantiopure Camphor-Based Di-, Tri- and Tetrasulfides", Heterocycles 1999, 51, 505-512.

S. Bruns, G. Haufe: "Catalytic Asymmetric Ring Opening of Epoxides to Chlorohydrins with Mild Chloride Donors and Enantiopure Titanium Complexes", Tetrahedron: Asymm. 1999, 10, 1563-1569.

A.A. Bogatschev, L.S. Kobrina, O.G.J. Meyer, G. Haufe: "Diels-Alder Reactions of Polyfluorinated 2,4-Cyclohexadienones with a- and b-Fluorostyrenes" J. Fluorine Chem. 1999, 97, 135-143.

K.W. Laue, C. Mück-Lichtenfeld, G. Haufe: "Enantioselective Syntheses of 2-Amino-4-fluoropent-4-enoic Acids. Isosteres of Asparagine", Tetrahedron 1999, 55, 10413-10424.

J. Oldendorf, G. Haufe: "Synthesis of g-Fluoro-a,b-unsaturated Carboxylic Esters from Saturated a-Fluoro Aldehydes", J. Prakt. Chem. 2000, 342, 52-57.

K.L. Kirk, B. Jayachandran, B. Herbert, S.-F. Lu, W.L. Padgett, J.W. Daly, G. Haufe, K.W. Laue: "Chemical and Biological Approaches to Non-Racemic Fluorinated Catecholamines and Amino Acids", ACS Symposium Series, Vol 746 , P. V. Ramachandran, Ed., American Chemical Society, Washington, D. C., 2000, pp 194-209.

F. Tranel, G. Haufe: "Lipase-catalyzed Resolution of 2-Fluorodecanoic Acid", Tetrahedron: Asymmetry 2000, 11, 889-896.

M. Lübke, R. Skupin, G. Haufe: "Regioselectivity of bromofluorination of functionalized 1-alkenes", J. Fluorine Chem. 2000, 102, 125-135.

S.-F. Lu, G. Haufe, K.W. Laue, W.L. Padgett, O. Oshunleti, J.W. Daly, K.L. Kirk: "Syntheses of (R)- and (S)-2- and 6-Fluoronorepinephrine and (R)- and (S)-2- and 6-Fluoro-epinephrine: Effect of Stereochemistry on Fluorine-Induced Adrenergic Selectivities", J. Med. Chem. 2000, 43, 1611-1619.

M. Runge, D. O'Hagan, G. Haufe: "Lipase-catalysed Polymerisation of Fluorinated Lactones and Fluorinated Hydroxycarboxylic Acids", J. Polym. Sci. A, Polym. Chem. 2000, 38, 2004-2012.

V.N. Kovtonyuk, L.S. Kobrina, Yu. V. Gatilov, I.Yu. Bagryanskaya, R. Fröhlich, G. Haufe: "Reactions of Polyfluorinated Cyclohexadienones with Diazoalkanes. I. Formation of Cyclopropanes from Polyfluorinated 2,4-Cyclohexadienones with Diazomethane and Phenyldiazomethane", Chem. Soc., Perkin Trans. 1, 2000, 1929-1933.

T. Takahashi, A. Fukushima, Y. Tanaka, M. Segawa, H. Hori, Y. Takeuchi, A. Burchardt, G. Haufe: "New Efficient Derivatizing Agent, a-Cyano-a-fluoro(2-naphthyl)acetic Acid (2-CFNA). Application on the ee Determination of (-)-3-Acetoxy-2-fluoro-2-(hexadecyloxy)propan-1-ol", CHIRALITY 2000, 12, 458-463.

S. Bruns, G. Haufe: "Enantioselective introduction of Fluoride into Organic Compounds. First Asymmetric Ring Opening of Epoxides by Hydrofluorinationg Reagents. J. Fluorine Chem. 2000,104, 247-254.

W.-R. Abraham, H.-A. Arfmann, K. Kieslich, G. Haufe: "Regioselectivity of the Microbial Hydroxylation of Nortricyclanol and its Derivatives", Biocatalysis & Biotransformation 2000, 18, 283-290.

O.G.J. Meyer, R. Fröhlich, G. Haufe: "Asymmetric Cyclopropanation of Vinyl Fluorides: Access to Enantiopure Monofluorinated Cyclopropane Carboxylates", Synthesis 2000, 1479-1490.

K.W. Laue, S. Kröger, E. Wegelius, G. Haufe: "Stereoselective Synthesis of g-Fluorinated a-Amino Acids using 2-Hydroxy-3-pinanone as an Auxiliary", Eur. J. Org. Chem. 2000, 3737-3743.

M. Runge, G. Haufe: "Synthesis of a Fluorinated Analogue of the Antibiotic Lasiodiplodin", J. Org. Chem. 2000, 63, 8737-8742.

Dissertations:

Dörthe Wölker: "Stereoselective Synthese und Biotransformation fluorierter cyclischer N-Phenylcarbamate mit Beauveria bassiana".

Stefan Bruns: "Katalytische asymmetrische Epoxidringöffnung zu Chlor- und Fluorhydrinen".

Martina Runge: "Naturstoffanaloge monofluorierte Macrolide. Synthesen und Reaktionen".

Oliver G.J. Meyer: "Stereoselektive Cyclopropanierung von Vinylfluoriden"