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  • 1
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    Organocatalysis (2008)
    Berlin, Heidelberg : Springer
    Details
    Keywords: Biochemistry ; Chemistry, Organic
    ISBN: 9783540734956
    URL: https://doi.org/10.1007/978-3-540-73495-6
    Language: English
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  • 2
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    Proline-catalysed Mannich reactions of acetaldehyde (2008)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2008-02-22
    Description: Small organic molecules recently emerged as a third class of broadly useful asymmetric catalysts that direct reactions to yield predominantly one chiral product, complementing enzymes and metal complexes. For instance, the amino acid proline and its derivatives are useful for the catalytic activation of carbonyl compounds via nucleophilic enamine intermediates. Several important carbon-carbon bond-forming reactions, including the Mannich reaction, have been developed using this approach, all of which are useful for making chiral, biologically relevant compounds. Remarkably, despite attempts, the simplest of all nucleophiles, acetaldehyde, could not be used in this way. Here we show that acetaldehyde is a powerful nucleophile in asymmetric, proline-catalysed Mannich reactions with N-tert-butoxycarbonyl (N-Boc)-imines, yielding beta-amino aldehydes with extremely high enantioselectivities-desirable products as drug intermediates and in the synthesis of other biologically active molecules. Although acetaldehyde has been used as a nucleophile in reactions with biological catalysts such as aldolases and thiamine-dependent enzymes, and has also been employed indirectly, its use as an inexpensive and versatile two-carbon nucleophile in asymmetric, small-molecule catalysis will find many practical applications.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Yang, Jung Woon -- Chandler, Carley -- Stadler, Michael -- Kampen, Daniela -- List, Benjamin -- England -- Nature. 2008 Mar 27;452(7186):453-5. doi: 10.1038/nature06740. Epub 2008 Feb 20.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mulheim an der Ruhr, Germany.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/18288105" target="_blank"〉PubMed〈/a〉
    Keywords: Acetaldehyde/*chemistry ; Biological Products/chemical synthesis/chemistry ; Carbon/chemistry ; Catalysis ; Imines/chemistry ; Mannich Bases/*chemistry ; Molecular Structure ; Peptides/chemical synthesis/chemistry ; Pharmaceutical Preparations/chemical synthesis/chemistry ; Proline/*chemistry
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 3
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    Immune versus natural selection: antibody aldolases with enzymic rates but broader scope (1998)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 1998-02-12
    Description: Structural and mechanistic studies show that when the selection criteria of the immune system are changed, catalytic antibodies that have the efficiency of natural enzymes evolve, but the catalytic antibodies are much more accepting of a wide range of substrates. The catalytic antibodies were prepared by reactive immunization, a process whereby the selection criteria of the immune system are changed from simple binding to chemical reactivity. This process yielded aldolase catalytic antibodies that approximated the rate acceleration of the natural enzyme used in glycolysis. Unlike the natural enzyme, however, the antibody aldolases catalyzed a variety of aldol reactions and decarboxylations. The crystal structure of one of these antibodies identified the reactive lysine residue that was selected in the immunization process. This lysine is deeply buried in a hydrophobic pocket at the base of the binding site, thereby accounting for its perturbed pKa.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Barbas, C F 3rd -- Heine, A -- Zhong, G -- Hoffmann, T -- Gramatikova, S -- Bjornestedt, R -- List, B -- Anderson, J -- Stura, E A -- Wilson, I A -- Lerner, R A -- CA27489/CA/NCI NIH HHS/ -- New York, N.Y. -- Science. 1997 Dec 19;278(5346):2085-92.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/9405338" target="_blank"〉PubMed〈/a〉
    Keywords: Animals ; Antibodies, Catalytic/chemistry/immunology/*metabolism ; Binding Sites ; Catalysis ; Crystallography, X-Ray ; Decarboxylation ; *Evolution, Molecular ; Fructose-Bisphosphate Aldolase/chemistry/immunology/*metabolism ; Glycolysis ; Hydrogen-Ion Concentration ; Immunization ; Immunoglobulin Fab Fragments/chemistry/immunology/*metabolism ; Kinetics ; Lysine/chemistry/metabolism ; Mice ; Models, Molecular ; Protein Conformation ; Pyridoxal/metabolism ; Selection, Genetic ; Substrate Specificity
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
    Published by American Association for the Advancement of Science (AAAS)
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  • 4
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    Asymmetric spiroacetalization catalysed by confined Bronsted acids (2012)
    Nature Publishing Group (NPG)
    Details
    Publication Date: 2012-03-17
    Description: Acetals are molecular substructures that contain two oxygen-carbon single bonds at the same carbon atom, and are used in cells to construct carbohydrates and numerous other molecules. A distinctive subgroup are spiroacetals, acetals joining two rings, which occur in a broad range of biologically active compounds, including small insect pheromones and more complex macrocycles. Despite numerous methods for the catalytic asymmetric formation of other commonly occurring stereocentres, there are few approaches that exclusively target the chiral acetal centre and none for spiroacetals. Here we report the design and synthesis of confined Bronsted acids based on a C(2)-symmetric imidodiphosphoric acid motif, enabling a catalytic enantioselective spiroacetalization reaction. These rationally constructed Bronsted acids possess an extremely sterically demanding chiral microenvironment, with a single catalytically relevant and geometrically constrained bifunctional active site. Our catalyst design is expected to be of broad utility in catalytic asymmetric reactions involving small and structurally or functionally unbiased substrates.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Coric, Ilija -- List, Benjamin -- England -- Nature. 2012 Mar 14;483(7389):315-9. doi: 10.1038/nature10932.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mulheim an der Ruhr, Germany.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/22422266" target="_blank"〉PubMed〈/a〉
    Keywords: Acetals/*chemical synthesis/*chemistry ; Animals ; Biological Products/*chemical synthesis/*chemistry/pharmacology ; Catalysis ; Catalytic Domain ; Female ; Male ; Models, Molecular ; Molecular Conformation ; Phosphoric Acids/*chemistry ; Sex Attractants/chemical synthesis/chemistry/pharmacology ; Stereoisomerism ; Thermodynamics
    Print ISSN: 0028-0836
    Electronic ISSN: 1476-4687
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Published by Nature Publishing Group (NPG)
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  • 5
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    Chemistry. The organic approach to asymmetric catalysis (2006)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2006-09-16
    Description: 〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉List, Benjamin -- Yang, Jung Woon -- New York, N.Y. -- Science. 2006 Sep 15;313(5793):1584-6.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Max-Planck Institut fur Kohlenforschung, 45470 Mulheim an der Ruhr, Germany. list@mpi-muelheim.mpg.de〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/16973867" target="_blank"〉PubMed〈/a〉
    Keywords: Amino Acids/chemical synthesis ; *Catalysis ; Chemistry, Pharmaceutical ; Drug Design ; Organic Chemicals/*chemistry ; Stereoisomerism
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
    Published by American Association for the Advancement of Science (AAAS)
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  • 6
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    Organotextile catalysis (2013)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2013-09-14
    Description: Throughout human history, textiles have been integral to daily life, but their exploration in catalysis has been rare. Herein, we show a facile and permanent immobilization of organocatalysts on the textile nylon using ultraviolet light. The catalyst and the textile material require no chemical modification for the immobilization. All of the prepared textile-immobilized organocatalysts (a Lewis basic, a Bronsted acidic, and a chiral organocatalyst) display excellent stability, activity, and recyclability for various organic transformations. Very good enantioselectivity (〉95:5 enantiomeric ratio) can be maintained for more than 250 cycles of asymmetric catalysis. Practical and straightforward applications of textile organocatalysis may be beneficial for various fields by offering inexpensive and accessible functionalized catalytic materials.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Lee, Ji-Woong -- Mayer-Gall, Thomas -- Opwis, Klaus -- Song, Choong Eui -- Gutmann, Jochen Stefan -- List, Benjamin -- New York, N.Y. -- Science. 2013 Sep 13;341(6151):1225-9. doi: 10.1126/science.1242196.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Max-Planck-Institut fur Kohlenforschung, Mulheim an der Ruhr, Germany.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/24031014" target="_blank"〉PubMed〈/a〉
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
    Published by American Association for the Advancement of Science (AAAS)
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  • 7
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    Asymmetric Lewis acid organocatalysis of the Diels-Alder reaction by a silylated C-H acid (2016)
    American Association for the Advancement of Science (AAAS)
    Details
    Publication Date: 2016-02-27
    Description: Silylium ion equivalents have shown promise as Lewis acid catalysts for a range of important C-C bond-forming reactions. Here we describe chiral C-H acids that upon in situ silylation, generate silylium-carbanion pairs, which are extremely active Lewis acid catalysts for enantioselective Diels-Alder reactions of cinnamates with cyclopentadiene. Enantiomeric ratios of up to 97:3 and diastereomeric ratios of more than 20:1 are observed across a diverse set of substitution patterns with 1 mole percent (mol %) of C-H acid catalyst and 10 mol % of a silylating reagent. The results show promise for broad applications of such C-H acid-derived silylium ion equivalents in asymmetric Lewis acid catalysis.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Gatzenmeier, Tim -- van Gemmeren, Manuel -- Xie, Youwei -- Hofler, Denis -- Leutzsch, Markus -- List, Benjamin -- New York, N.Y. -- Science. 2016 Feb 26;351(6276):949-52. doi: 10.1126/science.aae0010.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mulheim an der Ruhr, Germany. ; Max-Planck-Institut fur Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mulheim an der Ruhr, Germany. list@kofo.mpg.de.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/26917765" target="_blank"〉PubMed〈/a〉
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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  • 8
    Electronic Resource
    Electronic Resource
    Highly stereoselective synthesis of tetrasubstituted alkenes via [2,3]-wittig rearrangement
    Amsterdam : Elsevier
    Tetrahedron Letters 35 (1994), S. 9021-9024 
    Details
    ISSN: 0040-4039
    Keywords: 3]-Wittig rearrangement ; Claisen rearrangement ; Horner-Wadsworth-Emmons reaction ; [2 ; tetrasubstituted alkenes
    Source: Elsevier Journal Backfiles on ScienceDirect 1907 - 2002
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://linkinghub.elsevier.com/retrieve/pii/0040-4039(94)88416-1
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    Paper (German National Licenses)
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  • 9
    Electronic Resource
    Electronic Resource
    Über die Mikrostruktur von Kobalt-Katalysatoren (1955)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 38 (1955), S. 960-971 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Es wurden an verschiedenen Kobalt-Katalysatoren auf Silicagel- und Kieselgurbasis, wie sie in der Kohlenoxydhydrierung nach Fischer-Tropsch Verwendung finden, die Oberfläche und insbesondere die Porenverteilung mit Hilfe der Tieftemperatur-Adsorptions-Desorptionsisothermen bestimmt.
    Additional Material: 11 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19550380416
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  • 10
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    Aldol sensors for the rapid generation of tunable fluorescence by antibody catalysis (1998)
    National Academy of Sciences
    Details
    Publication Date: 1998-12-22
    Print ISSN: 0027-8424
    Electronic ISSN: 1091-6490
    Topics: Biology , Medicine , Natural Sciences in General
    Published by National Academy of Sciences
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