Fachbereich 12 - Chemie und Pharmazie
Organisch-Chemisches Institut
Professor Dr. Günter Haufe

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 Mehrfachbindungssysteme", European Graduate College "Template Directed Chemical Synthesis", Fonds der Chemischen Industrie, Volkswagen-Stiftung, DAAD, Ministry of Education, Science, Sports and Cultute, Japan, Merck KGaA.

Veröffentlichungen:

A. Burchardt, T. Takahashi, Y. Takeuchi, G. Haufe, "Synthesis of a Fluorinated Analogue of Anticancer Active Ether Lipids", J. Org. Chem. 2001, 66, 2078-2084.

M. Essers, B. Wibbeling, G. Haufe, "Synthesis of the First Fluorinated Cantharidine Analogue", Tetrahedron Lett. 2001, 42, 5429-5433.

T. Ernet, A. Maulitz, E.-U. Würthwein, G. Haufe, "Chemical Consequences of Fluorine Substitution. Part 1. Experimental and Theoretical Results on Diels-Alder Reactions of a- and b-Fluorostyrenes", J. Chem. Soc., Perkin Trans. 1 2001, 1929-1938.

G. Haufe, S. Bruns, M. Runge, "Enantioselective Ring-opening of Epoxides by HF-Reagents. Asymmetric Synthesis of Fluoro Lactones", J. Fluorine Chem. 2001, 112, 55-61.

G. Haufe, A. Burchardt, "Synthesis of a Fluorinated Ether Lipid Analogous to a Platelet Activating Factor", Eur. J. Org. Chem. 2001, 4501-4507.

F. Chanteau, M. Essers, R. Plantier-Royon, G. Haufe and C. Portella, “Dienophilic reactivity of perfluoroalkenyl ketones in Diels-Alder reactions“, Tetrahedron Lett. 2002, 43, 1677-1680.

M. Fix, S. Wiehle, G. Haufe, and H.-J. Galla, “Synthesis of regioisomeric fluorohydroxylated fatty acid methyl esters and their phase behavior at the air-water interface compared to hydroxylated amphiphiles“, Colloids Surfaces A: Physicochem. Engin. Aspects 2002 198-200, 151-164.

S. Bruns and G. Haufe, “(Salen)chromium Complex Mediated Asymmetric Ring Opening of Meso- and Racemic Epoxides with Different Fluoride Sources“, Adv. Synth. & Catal. 2002, 344, 165-171.

G. Haufe, A. Burchardt, “Improved Synthesis of Fluorinated Analogues of Anticancer Active Ether Lipids“, Synthesis 2002, 648-654.

D. Wölker and G. Haufe, “Synthesis of Optically Active Vicinal Fluorohydrins by Lipase-catalyzed Deracemization“, J. Org. Chem. 2002, 67, 3015-3021.

G. Haufe, D. Wölker and R. Fröhlich, “Selectivity of Biohydroxylation with Beauveria bassiana of trans-2-Fluorocycloalkyl-N-phenylcarbamates“, J. Org. Chem. 2002, 67, 3022-3028.

G. Haufe, T. C. Rosen, O. G. J. Meyer, R. Fröhlich, K. Rissanen, “Synthesis, Reactions and Structural Features of Monofluorinated Cyclopropane Carboxylates“, J. Fluorine Chem. 2002, 114, 189-198.

M. Essers, C. Mück-Lichtenfeld and G. Haufe, “Deastereoselective Diels-Alder Reactions of a-Fluorinated a,b-Unsaturated Carbonyl Compounds. Chemical consequences of Fluorine Substitution. Part 2.“, J. Org. Chem. 2002, 67, 4715-4721.

C. E. Uhlemann, C. G. Pfaff, G. Hägele, K. W. Laue, M. Lübke and G. Haufe, “The frist automated 470.59 MHz 19F NMR-controlled titration. Dissozciation constants and ion-specific chemical shifts of 2-amino-4-fluoro-2-methylpent-4-enoic acid“, Magn. Res. Chem. 2002, 40, 573-580.

G. Haufe, O. G. J. Meyer and C. Mück-Lichtenfeld, “Addition of Dihalocarbenes to Vinyl Fluorides. Chemical Consequences of Fluorine Substitution. Part 3.“, Coll. Czech. Chem. Comm. 2002, 67, 1493-1504.

S. Grimme, A. Bahlmann and G. Haufe, “Ab initio Calculations for the Optical Rotations of Conformationally Flexible Molecules: A Case Study on Six-, Seven- and Eight-membered Fluorinated Cycloalkanol Esters“, Chirality, 2002, 14, 793-797.

T. C. Rosen and G. Haufe, “Synthesis of Enantiopure, Monofluorinated Phenylcyclopropyl Derivatives by Lipase-catalyzed Kinetic Resolution“, Tetrahedron:Asymmetry 2002, 13, 1397-1405.

M. Essers and G. Haufe, “Chemical Consequences of Fluorine Substitution. Part 4. Diels-Alder Reactions of Fluorinated p-Bezoquinones with Dane's Diene. Synthesis of Fluorinated D-Homosteroids“, J. Chem. Soc., Perkin Trans. I 2002, 2719-2728

DISSERTATIONS:

Frank Tranel: "[3,3]-Sigmatrope Umlagerungen von Vinylfluoriden

Holger Schimanski: "Transannulare O-Heterocyclisierungen zwölfgliedriger 1,5-Diene als Basis für Synthesen von Acetogeninen aus Annonaceae"

Michael Essers: "Diels-Alder-Reaktionen fluorierter Dienophile und Diene und ihr Einsatz in Synthesen fluorierter Steroid-Analoga und Cantharidine"

Jens Oldendorf: "Enantioselektive Synthese fluorierter Dihydroceramide“

Martin Lübke: "Synthese monofluorierter Aminosäuren. Bausteine für biologisch aktive Verbindungen“