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Organometallic Chemistry

The research in the Department of Organometallic Chemistry is focused on the development and understanding of organometallic reagents and catalysts, as well as on their application to the synthesis of structurally complex targets of biological significance. Particular attention is paid to the development and validation of catalytic methods for C-C-bond formation. Long term projects of current interest concern alkene and alkyne metathesis, the development and use of pi-acids (platinum, gold etc.), iron catalysis and cross coupling in general.

Moreover, the group is engaged in the development of novel donor ligands, including carbenes and compounds containing formally "zerovalent" carbon atoms. All methods are scrutinized by applications to the total synthesis and "diverted total synthesis" of natural products and pharmaceutically active compounds.

Alois Fürstner

Prof. Dr. Alois Fürstner

2009-2011
Managing Director of the Max-Planck-Institut für Kohlenforschung
since 1998
Director at the Max-Planck-Institut für Kohlenforschung and Professor at the Technical University of Dortmund
1993-1998
Group leader at the Max-Planck-Institut für Kohlenforschung and Lecturer at the University of Dortmund
1992
“Habilitation” in Organic Chemistry at the Technical University Graz, Austria
1990-1991
Postdoctoral fellow at the University of Geneva, Switzerland (W. Oppolzer)
1987
PhD at the Technical University Graz, Austria (H. Weidmann)
1962
born in Bruck/Mur (Austria)
2014
Gay-Lussac-Humboldt Prize
2014
Hans Herloff Inhoffen Medal
2013
Kitasato Medal, Tokyo, Japan
2013
Karl Ziegler Prize of the German Chemical Society
2013
Prix Jaubert of the University of Geneva
2011
Prelog Medal, ETH Zurich, Switzerland
2011
Lilly European Distinguished Lectureship Award
2008
Janssen Pharmaceutica Prize for Creativity in Organic Synthesis
2006
Heinrich Wieland Prize
2006
Otto Bayer Prize
2005
Mukaiyama Award, Society of Synthetic Organic Chemistry, Japan
2005
Junior Award, International Society of Heterocyclic Chemistry
2004
Tetrahedron Chair
since 2004
Corresponding Member of the Österreichische Akademie der Wissenschaften
since 2004
Member of the Nordrhein-Westfälische Akademie der Wissenschaften
2004
Centenary Lecture, Royal Society of Chemistry
2002
Arthur C. Cope Scholar Award, American Chemical Society
2002
Merck Academic Development Program Award
since 2002
Member of the Deutsche Akademie der Naturforscher Leopoldina
2001
Victor Grignard - Georg Wittig Prize, Société Française de Chimie
2000
AstraZeneca Award in Organic Chemistry
2000
Thieme-IUPAC Prize in Synthetic Organic Chemistry
1999
Leibniz Award, German Science Foundation (DFG)
1999
Invited Professor at the Ecole Normale Supérieure, Paris, France
1998
Ruhr Prize for Arts and Sciences, Mülheim/Ruhr
1994
Invited Professor at the Université Claude Bernard - Lyon I, France
1994
Lecturer's scholarship ("Dozentenstipendium"), Fonds der Chemischen Industrie
2014
Chairman of BOSS-XIV, Louvain-la-Neuve, Belgium
since 2014
Chairman of the Editorial Board of "Angewandte Chemie"
since 2014
Senior Editor "Bulletin of the Chemical Society of Japan" (BCSJ)
since 2012
Member of the Scientific Advisory Board at the Institute of Chemical Research of Catalonia (ICIQ)
since 2010
Member of the Selection Committee of the Heinrich Wieland Prize
since 2008
Member of the Editorial Board of "Science of Synthesis" (formerly "Houben-Weyl")Knowledge Updates
2008
Member of the Search Committee, Institute of Science and Technology Austria (ISTA)
since 2007
Member of the Selection Committee of the Otto-Hahn-Prize of the GdCH
2006-2010
Chairman of the Selection Committee of the Alexander von Humboldt-Foundation, Feodor-Lynen-Program
2004-2011
Member of the Board of Governors of the Gesellschaft Deutscher Chemiker (GDCh)
2002-2010
Member of the Selection Committee of the Alexander von Humboldt-Foundation, Feodor-Lynen-Program
2002-2009
Member of the Scientific Advisory Board at the Institut für Organische Katalyseforschung Rostock, since 2003 Leibniz-Institute for Organic Catalysis at the University of Rostock
2001-2007
Scientific Editor of "Chemical Communications"
2001-2006
Member of the Board of Editors of "Organic Syntheses"
 

since 2013     Member of the Editorial Board "Comptes Rendus Chimie"
since 2012     Member of the International Advisory Board of "ChemPlusChem"
since 2010     Member of the Editorial Board „Angewandte Chemie" and of the Advisory Board
                    "Israel Journal of Chemistry"
since 2009     Member of the Advisory Board "ChemCatChem"
2009-2013     Member of the Advisory Board "Synthesis" and "Synlett"
since 2007     Member of the Advisory Board "Nachrichten aus der Chemie"
since 2006     Member of the Advisory Boards "ChemMedChem"
since 2005     Member of the Editorial Advisory Board "Progress in Heterocylic Chemistry"
2002-2004     Member of the Editorial Advisory Board "Journal of Organic Chemistry“
since 2000     Member of the Advisory Board "Advanced Synthesis & Catalysis"
since 1997     Member of the Editorial Board "Topics in Organometallic Chemistry"

2014     Siegfried-Hünig Lecture (Germany)
2013     Elhuyar-Goldschmidt Lecture (Spain)
2012     First Novartis Eastern Europe Lectureship (Russia, Poland)
2012     Durham University Musgrave Lecture (United Kingdom)
2011     Lilly European Distinguished Lectureship (Greece)
2009     Astellas Lecture (Japan)
2008     Sir Robert Robinson Distinguished Lecture (United Kingdom)
2008     Westschweizer Graduierten Kolleg (3ème Cycle) (Switzerland)
2008     Andrew Derome Lecture (United Kingdom)
2007     Eli Lilly Lecture (USA)
2007     Roessler Lecture Series (USA)
2007     Pfizer Michigan Tour (USA)
2005     Abbott Process Chemistry Lecture (USA)
2005     Bristol-Myers Squibb Lecture (USA)
2004     Merck Frosst Lecture (Canada)
2004     Wyeth Lecture (USA)
2004     Merck Lecture (United Kingdom)
2004     Centenary Lecture der Royal Society of Chemistry (United Kingdom)
2003     Bristol-Myers Squibb Lecture (USA)
2002     Novartis Central Europe Lectureship (Czech Republik, Slovakia, Hungary)
2001     Victor Grignard - Georg Wittig Lecture (France)
2000     Holm Lecture (Denmark)
1999     Bürgenstock (Schweiz)
1999     Organic Reactions Lectureship (USA)
1999     Merck-Frosst Lecture (Canada)
1999     16th H. C. Brown Lecturer (Canada)
1999     Smith-Kline Lecture (USA)
1997     Novartis Lectureship (Switzerland)
1997     Nozaki Lecture (Japan)

Research Topics

Alkyne Metathesis
Alkyne Metathesis

Alkyne Metathesis

Whereas alkene metathesis is a striking success in the catalytic arena and was rapidly embraced by the synthetic community, the related metathesis of alkynes is much less commonly used. However, the reaction has several assets: it benefits from a surprisingly strong driving force and is mechanistically well understood; alkyne metathesis is unambiguous in its stereochemical consequences when combined with controlled semi-reduction; alkynes are amenable to a large variety of post-metathesis transformations, most notably by activation with carbophilic Lewis acid catalysts.

Our group is committed to demonstrate the remarkable performance of this transformation in synthesis. To this end, we are engaged in the development of new alkyne metathesis catalysts and in understanding their mode of action. The latest generation of catalysts described by our group is molybdenum-nitrides and molybdenum-alkylidynes endowed with silanolate ligands. These complexes combine a previously unknown level of reactivity with an exquisite functional group tolerance. At the same time, they can easily be rendered air stable, which makes them highly practical and user-friendly.

In parallel work, our group is constantly probing and expanding the preparative scope of alkyne metathesis by applications to structurally complex and biologically relevant target molecules. The projects encompass prostaglandins, peptides, alkaloids, macrolide antibiotics and various anti-cancer agents. Prominent examples in the past were epothilone, the latrunculins, cruentaren A, amphidinolide V, the ecklonialactones, and lactimidomycin.
 

Download Alkyne Metathesis

Alkene Metathesis
Alkene Metathesis

Alkene Metathesis

The keen interest in alkene metathesis dates back to the outset of Prof. Fürstner's independent career in the early 1990s. Our initial work showed the outstanding performance of the then brand new molybdenum and ruthenium alkylidene complexes developed by Schrock and Grubbs, respectively, for the preparation of medium-sized and macrocyclic rings. Rules were spelled out how to implement ring closing metathesis into retrosynthetic planning and examples were given, which demonstrated the complementary logic of this transformation.

Subsequent work aimed at the development of readily accessible and even more efficient catalysts (ruthenium allenylidenes and -indenylidenes, “second generation” ruthenium carbenes endowed with NHC ligands etc.), some of which are now commercially available. A rapid parallel assay was established to test the performance of new catalysts by IR thermography. Moreover, the first examples of metathesis reactions in supercritical carbon dioxide were reported, which showed the advantages of this particular medium in the formation of macrocyclic fragrance ingredients as well as in ROMP polymerizations.

Significant efforts are made to demonstrate the strategic advantages of alkene metathesis for advanced organic synthesis. Starting from early work on macrocyclic musk, the group has gone on to the total synthesis of highly complex polyketides, alkaloids, terpenes, and glycolipids.

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π-Acid Catalysis
π-Acid Catalysis

π-Acid Catalysis

Catalysis based on the activation of p-systems with the aid of carbophilic Lewis acids such as Pt(2+) and Au(1+) has gained considerable momentum. Except for a few pioneering studies, this field was virtually inexistent until the late 1990’s but is currently one of the most rapidly growing areas of homogeneous catalysis.

As early as 1998, the Fürstner group proposed a unifying mechanism, which guided our investigations during the following years. This hypothesis-driven approach led to the discovery of several new reactions, which were successfully scrutinized by several natural product total syntheses. Moreover, we are dedicated to the characterization of pertinent reactive intermediates to refine the mechanistic understanding for gold and platinum catalysis. Likewise, the development of practical asymmetric variants is actively pursued.

Download Noble Metal Catalysis

Iron Catalysis
Iron Catalysis

Iron Catalysis

We are interested in the development of catalysts based on cheap, non-toxic, benign and readily available transition metals as substitutes for traditional noble metal complexes. Although not limited to, iron catalysis is prominently featured in this context.

Particular attention is paid to the development of iron catalysts for cross coupling, cycloisomerization reactions, cycloadditions of unactivated substrates, and carbometalations of π-bonds. Considerable efforts are made to identify, isolate and characterize short-lived and, in part, highly reactive organoiron intermediates to gain a better understanding for the largely unknown mechanisms of such iron-catalyzed C-C bond-forming reactions. Applications of the new methods to the preparation of relevant target molecules complement our portfolio.

Download Iron Catalysis

Novel Concepts for Catalysis
Novel Concepts for Catalysis

Novel Concepts for Catalysis

Various lines of research are pursued by which we intend to establish new principles for catalysis and to develop conceptually novel ligand architectures.

Redox Catalysis:
We are striving to replace notoriously stoichiometric reactions of proven versatility by catalytic processes. Successful examples are the first Nozaki-Hiyama-Kishi (NHK) reactions catalytic in chromium as well as carbonyl coupling reactions catalytic in titanium. The latter opened a new entry into indoles and various other types of aromatic heterocycles.

Cross Coupling:
Our group has introduced the “9-methoxy-9-BBN variant” of the Suzuki reaction as a highly versatile and base-free procedure for cross coupling. Moreover, an improved method for Stille-Migita reactions was recently described, which is applicable to polyfunctionalized and sensitive substrates.

Download Diverse Methods

Carbene Ligands:
Whereas the σ-donor qualities of N-heterocyclic carbenes (NHC's) are undisputed and extensively used in homogeneous catalysis, the π-acceptor properties of such ligands are often considered negligible. However, recent studies from this laboratory showed that the acceptor properties of NHCs can be up-regulated to the extent that they start dictating the observed reactivity. Therefore the general perception of this important class of ligands may need to be revised. Moreover, we proposed several alternative design principles for stable singlet carbenes, including amino-ylide carbenes (AYC’s), carbenes stabilized by lateral enamines, and push-pull carbene structures.

Coordination Chemistry at Carbon:
Organic molecules are commonly understood as substances based on carbon atoms which involve all four valence electrons in bonding. If two electrons form a lone-pair, one crosses the traditional borders to coordination chemistry and/or enters the realm of reactive intermediates. Compounds, wherein a carbon atom configures all four valence electrons in form of two lone-pairs may seem elusive at first sight. Following insightful early reports and recent computational studies, however, our group is investigating the preparation and reactivity of compounds, in which carbon serves as the central atom of a complex. The description of certain carbogenic materials as coordination compounds differs fundamentally from the common understanding of organic chemistry.

Download Novel Ligands

Total Synthesis and Evaluation of Natural Products
Total Synthesis and Evaluation of Natural Products

Total Synthesis and Evaluation of Natural Products

A significant part of our work is dedicated to the application of organometallic catalysis to the total synthesis of structurally complex natural products of biological significance; where indicated, we are also committed to prepare analogues by “diverted total synthesis” for further evaluation.

From the chemical viewpoint, all projects intend to scrutinize the synthetic methods of interest to our group. We wish to develop syntheses that are concise, convergent, productive and scalable; ideally, they should be largely catalysis-based and require a minimum of protecting group manipulations. With regard to the targets, our choice is based on considerations of structural complexity, biological activity, and non-availability of meaningful amounts from the natural sources. Biological assessments of the compounds prepared in the laboratory are carried out in close collaboration with external partners.

Download Selected Total Syntheses

 

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