Eric Meggers

Last updated

Eric Meggers (born 10 May 1968 in Bonn, Germany) is a German chemist and professor of organic chemistry and chemical biology at the University of Marburg, Germany. His research currently focuses on the design of chiral catalysts for stereoselective synthesis.

Contents

Biography

Born in Bonn, Germany, Meggers studied chemistry at the University of Bonn and subsequently received his Ph.D. in 1999 under Bernd Giese at the University of Basel, Switzerland. After postdoctoral research at the Scripps Research Institute in La Jolla, USA, Meggers started his independent career in 2002 as assistant professor at the University of Pennsylvania, USA. Since 2007, Meggers is full professor of organic chemistry and chemical biology at the University of Marburg, Germany.

Research

Meggers specializes on exploiting metal-centered stereochemistry for applications in medicine, chemical biology, and asymmetric catalysis. [1] The research program started with the design of metal-based protein kinase inhibitors, [2] the subsequent design of chiral organocatalysts based on inert metal complexes (metal-templated organocatalysis), [3] and finally arrived at the current focal point of developing chiral transition metal catalysts featuring exclusively metal-centered chirality (chiral-at-metal catalysts). [4] [5]

Other unrelated previous research:

Related Research Articles

Enantioselective synthesis Form of chemical synthesis

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as: a chemical reaction in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric products in unequal amounts.

Jack Halpern was an inorganic chemist, the Louis Block Distinguished Service Professor of Chemistry at the University of Chicago. Born in Poland, he moved to Canada in 1929 and the United States in 1962.

Organocatalysis Method in organic chemistry

In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds. Because of their similarity in composition and description, they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved.

A carbometalation is any reaction where a carbon-metal bond reacts with a carbon-carbon π-bond to produce a new carbon-carbon σ-bond and a carbon-metal σ-bond. The resulting carbon-metal bond can undergo further carbometallation reactions or it can be reacted with a variety of electrophiles including halogenating reagents, carbonyls, oxygen, and inorganic salts to produce different organometallic reagents. Carbometalations can be performed on alkynes and alkenes to form products with high geometric purity or enantioselectivity, respectively. Some metals prefer to give the anti-addition product with high selectivity and some yield the syn-addition product. The outcome of syn and anti- addition products is determined by the mechanism of the carbometalation.

In chemistry, bis(oxazoline) ligands (often abbreviated BOX ligands) are a class of privileged chiral ligands containing two oxazoline rings. They are typically C2‑symmetric and exist in a wide variety of forms; with structures based around CH2 or pyridine linkers being particularly common (often generalised BOX and PyBOX respectively). The coordination complexes of bis(oxazoline) ligands are used in asymmetric catalysis. These ligands are examples of C2-symmetric ligands.

Asymmetric hydrogenation is a chemical reaction that adds two atoms of hydrogen to a target (substrate) molecule with three-dimensional spatial selectivity. Critically, this selectivity does not come from the target molecule itself, but from other reagents or catalysts present in the reaction. This allows spatial information to transfer from one molecule to the target, forming the product as a single enantiomer. The chiral information is most commonly contained in a catalyst and, in this case, the information in a single molecule of catalyst may be transferred to many substrate molecules, amplifying the amount of chiral information present. Similar processes occur in nature, where a chiral molecule like an enzyme can catalyse the introduction of a chiral centre to give a product as a single enantiomer, such as amino acids, that a cell needs to function. By imitating this process, chemists can generate many novel synthetic molecules that interact with biological systems in specific ways, leading to new pharmaceutical agents and agrochemicals. The importance of asymmetric hydrogenation in both academia and industry contributed to two of its pioneers — William Standish Knowles and Ryōji Noyori — being awarded one half of the 2001 Nobel Prize in Chemistry.

Chiral Lewis acids (CLAs) are a type of Lewis acid catalyst. These acids affect the chirality of the substrate as they react with it. In such reactions, synthesis favors the formation of a specific enantiomer or diastereomer. The method is an enantioselective asymmetric synthesis reaction. Since they affect chirality, they produce optically active products from optically inactive or mixed starting materials. This type of preferential formation of one enantiomer or diastereomer over the other is formally known as asymmetric induction. In this kind of Lewis acid, the electron-accepting atom is typically a metal, such as indium, zinc, lithium, aluminium, titanium, or boron. The chiral-altering ligands employed for synthesizing these acids often have multiple Lewis basic sites that allow the formation of a ring structure involving the metal atom.

Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry. The first organogold compound discovered was gold(I) carbide Au2C2, which was first prepared in 1900.

Within the area of organocatalysis, (thio)urea organocatalysis describes the use of ureas and thioureas to accelerate and stereochemically alter organic transformations. The effects arise through hydrogen-bonding interactions between the substrate and the (thio)urea. Unlike classical catalysts, these organocatalysts interact by non-covalent interactions, especially hydrogen bonding. The scope of these small-molecule H-bond donors termed (thio)urea organocatalysis covers both non-stereoselective and stereoselective applications.

The Tsuji–Trost reaction is a palladium-catalysed substitution reaction involving a substrate that contains a leaving group in an allylic position. The palladium catalyst first coordinates with the allyl group and then undergoes oxidative addition, forming the π-allyl complex. This allyl complex can then be attacked by a nucleophile, resulting in the substituted product.

In Lewis acid catalysis of organic reactions, a metal-based Lewis acid acts as an electron pair acceptor to increase the reactivity of a substrate. Common Lewis acid catalysts are based on main group metals such as aluminum, boron, silicon, and tin, as well as many early and late d-block metals. The metal atom forms an adduct with a lone-pair bearing electronegative atom in the substrate, such as oxygen, nitrogen, sulfur, and halogens. The complexation has partial charge-transfer character and makes the lone-pair donor effectively more electronegative, activating the substrate toward nucleophilic attack, heterolytic bond cleavage, or cycloaddition with 1,3-dienes and 1,3-dipoles.

Alfons Baiker Swiss Chemist specializing in Catalysis

Alfons Baiker is a Swiss Chemist specializing in Catalysis. Baiker studied chemistry at ETH Zurich. After obtaining his PhD in 1974 he followed several post-doctoral stays at various universities. In 1989 he became a full professor in catalysis and reaction engineering at ETH where he worked until his retirement in 2010.

Diimines are organic compounds containing two imine (RCH=NR') groups. Common derivatives are 1,2-diketones and 1,3-diimines. These compounds are used as ligands and as precursors to heterocycles. Diimines are prepared by condensation reactions where a dialdehyde or diketone is treated with amine and water is eliminated. Similar methods are used to prepare Schiff bases and oximes.

Hydrophosphination is the insertion of a carbon-carbon multiple bond into a phosphorus-hydrogen bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is influenced by the catalyst. Catalysts take many forms, but most prevalent are bases and free-radical initiators.

Krische allylation

The Krische allylation involves the enantioselective iridium-catalyzed addition of an allyl group to an aldehyde or an alcohol, resulting in the formation of a secondary homoallylic alcohol. The mechanism of the Krische allylation involves primary alcohol dehydrogenation or, when using aldehyde reactants, hydrogen transfer from 2-propanol. Unlike other allylation methods, the Krische allylation avoids the use of preformed allyl metal reagents and enables the direct conversion of primary alcohols to secondary homoallylic alcohols.

Cyclic alkyl amino carbenes

In chemistry, cyclic(alkyl)(amino)carbenes (CAACs) are a family of stable singlet carbene ligands developed by Prof. Guy Bertrand and his group in 2005 at UC Riverside. In marked contrast with the popular N-heterocyclic carbenes (NHC) which possess two "amino" substituents adjacent to the "carbene" center, CAACs possess one "amino" substituent and an sp3 carbon atom "alkyl". This specific configuration makes the CAACs very good σ-donors and π-acceptors when compared to NHCs. Moreover the reduced heteroatom stabilization of the carbene center in CAACs versus NHCs also gives rise to a smaller ΔEST.

In homogeneous catalysis, C2-symmetric ligands refer to ligands that lack mirror symmetry but have C2 symmetry. Such ligands are usually bidentate and are valuable in catalysis. The C2 symmetry of ligands limits the number of possible reaction pathways and thereby increases enantioselectivity, relative to asymmetrical analogues. C2-symmetric ligands are a subset of chiral ligands. Chiral ligands, including C2-symmetric ligands, combine with metals or other groups to form chiral catalysts. These catalysts engage in enantioselective chemical synthesis, in which chirality in the catalyst yields chirality in the reaction product.

Metal-ligand cooperativity (MLC) is a mode of reactivity in which a metal and ligand of a complex are both involved in the bond breaking or bond formation of a substrate during the course of a reaction. This ligand is an actor ligand rather than a spectator, and the reaction is generally only deemed to contain MLC if the actor ligand is doing more than leaving to provide an open coordination site. MLC is also referred to as "metal-ligand bifunctional catalysis." Note that MLC is not to be confused with cooperative binding.

Jin-Quan Yu is a Chinese-born American chemist. He is the Frank and Bertha Hupp Professor of Chemistry at Scripps Research, where he also holds the Bristol Myers Squibb Endowed Chair in Chemistry. He is a 2016 recipient of the MacArthur Fellowship, and is a member of the American Academy of Arts and Sciences, American Association for the Advancement of Science, and the Royal Society of Chemistry. Yu is a leader in the development of C–H bond activation reactions in organic chemistry, and has reported many C–H activation reactions that could be applicable towards the synthesis of drug molecules and other biologically active compounds. He also co-founded Vividion Therapeutics in 2016 with fellow Scripps chemists Benjamin Cravatt and Phil Baran, and is a member of the scientific advisory board of Chemveda Life Sciences.

Benjamin List German chemist (born 1968)

Benjamin List is a German chemist who is one of the directors of the Max Planck Institute for Coal Research and professor of organic chemistry at the University of Cologne. He co-developed organocatalysis, a method of accelerating chemical reactions and making them more efficient. He shared the 2021 Nobel Prize in Chemistry with David MacMillan "for the development of asymmetric organocatalysis".

References

  1. Meggers, Eric (2017-05-15). "Exploiting Octahedral Stereocenters: From Enzyme Inhibition to Asymmetric Photoredox Catalysis". Angewandte Chemie International Edition. 56 (21): 5668–5675. doi:10.1002/anie.201612516.
  2. Feng, Li; Geisselbrecht, Yann; Blanck, Sebastian; Wilbuer, Alexander; Atilla-Gokcumen, G. Ekin; Filippakopoulos, Panagis; Kräling, Katja; Celik, Mehmet Ali; Harms, Klaus; Maksimoska, Jasna; Marmorstein, Ronen (2011-04-20). "Structurally Sophisticated Octahedral Metal Complexes as Highly Selective Protein Kinase Inhibitors". Journal of the American Chemical Society. 133 (15): 5976–5986. doi:10.1021/ja1112996. ISSN   0002-7863. PMC   3076536 . PMID   21446733.
  3. Xu, Weici; Arieno, Marcus; Löw, Henrik; Huang, Kaifang; Xie, Xiulan; Cruchter, Thomas; Ma, Qiao; Xi, Jianwei; Huang, Biao; Wiest, Olaf; Gong, Lei (2016-07-20). "Metal-Templated Design: Enantioselective Hydrogen-Bond-Driven Catalysis Requiring Only Parts-per-Million Catalyst Loading". Journal of the American Chemical Society. 138 (28): 8774–8780. doi:10.1021/jacs.6b02769. ISSN   0002-7863. PMC   8103658 . PMID   27336458.
  4. Zhang, Lilu; Meggers, Eric (2017-02-21). "Steering Asymmetric Lewis Acid Catalysis Exclusively with Octahedral Metal-Centered Chirality". Accounts of Chemical Research. 50 (2): 320–330. doi:10.1021/acs.accounts.6b00586. ISSN   0001-4842. PMID   28128920.
  5. Huang, Xiaoqiang; Meggers, Eric (2019-03-19). "Asymmetric Photocatalysis with Bis-cyclometalated Rhodium Complexes". Accounts of Chemical Research. 52 (3): 833–847. doi:10.1021/acs.accounts.9b00028. ISSN   0001-4842.
  6. Meggers, Eric; Zhang, Lilu (2010-08-17). "Synthesis and Properties of the Simplified Nucleic Acid Glycol Nucleic Acid". Accounts of Chemical Research. 43 (8): 1092–1102. doi:10.1021/ar900292q. ISSN   0001-4842. PMID   20405911.
  7. Streu, Craig; Meggers, Eric (2006-08-25). "Ruthenium-Induced Allylcarbamate Cleavage in Living Cells". Angewandte Chemie International Edition. 45 (34): 5645–5648. doi:10.1002/anie.200601752. ISSN   1433-7851. PMID   16856188.
  8. Völker, Timo; Meggers, Eric (April 2015). "Transition-metal-mediated uncaging in living human cells — an emerging alternative to photolabile protecting groups". Current Opinion in Chemical Biology. 25: 48–54. doi:10.1016/j.cbpa.2014.12.021. PMID   25561021.