ChemCatChem

Cover image for Vol. 4 Issue 7

Special Issue: Organocatalysis

July 2012

Volume 4, Issue 7

Pages 885–1019

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Cover Picture: Flowing and Vibrant Organocatalysis (ChemCatChem 7/2012) (page 885)

      Prof. Pier Giorgio Cozzi and Prof. Yujiro Hayashi

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201290022

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      Curiosity kills the flu! The cover picture shows a “curious” cat on the prowl for new effective synthetic strategies for Oseltamivir (Tamiflu®) synthesis. The cat represents a new, effective CATalyst able to perform a reaction in a very effective way. The European project CATAFLU.OR (organocatalysis against flu) proposed a new domino reaction based on an organocatalytic approach to the synthesis of Tamiflu derivatives. The innovative objectives and the long-term vision of this successful project anticipated new approaches to organocatalysts, new reactions, and new synthetic methodologies. To celebrate the success of organocatalysis in proposing new effective syntheses of Oseltamivir, P. G. Cozzi and Y. Hayashi have invited a number of distinguished colleagues active in the organocatalytic field to show the potential of organocatalysis. As expressed in the editorial, on p. 887 ff., flowing and vibrant organocatalysis is illustrated by a series of articles collected in this issue, covering many aspects of the discipline.

  2. Back Cover

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Advances and Applications in Organocatalytic Asymmetric aza-Michael Addition (page 1020)

      Prof. Dr. Jun Wang, Prof. Dr. Pengfei Li, Pui Ying Choy, Prof. Dr. Albert S. C. Chan and Prof. Dr. Fuk Yee Kwong

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201290025

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      Asymmetric aza-Michael Addition The back cover shows an array of asymmetric organocatalysts and the C[BOND]N bond-containing enantioenriched products formed from nitrogen-based nucleophiles and a,bunsaturated carbonyl systems. In their “Minireview Advances and Applications in Organocatalytic Asymmetric aza-Michael Addition” on p. 917 ff., F. Y. Kwong, A. S. C. Chan, P. Li et al. describe progress in the field of inter- and intramolecular aza-Michael additions, covering catalysis with primary and secondary amines and Brnsted acids, as well as miscellaneous catalyst systems, such as cinchona alkaloid derivatives and phase-transfer catalysts.

  3. Editorial

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Flowing and Vibrant Organocatalysis (pages 887–889)

      Prof. Pier Giorgio Cozzi and Prof. Yujiro Hayashi

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201200331

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      A bright start for a new beginning: Since the rediscovery of organocatalysis by List, MacMillan, Barbas, Jørgensen, Terada, Akiyama, and many others, organocatalysis has become a flowing and vibrant field of research.

  4. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Graphical Abstract: ChemCatChem 7/2012 (pages 890–895)

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201290023

  5. News

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Spotlights on our sister journals: ChemCatChem 7/2012 (pages 898–900)

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201290024

  6. Minireviews

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Organocatalytic Asymmetric Oxidations with Hydrogen Peroxide and Molecular Oxygen (pages 901–916)

      Dr. Alessio Russo, Claudia De Fusco and Prof. Dr. Alessandra Lattanzi

      Article first published online: 8 JUN 2012 | DOI: 10.1002/cctc.201200139

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      A friendly team! Different organic promoters have been successfully employed in asymmetric oxidations with hydrogen peroxide and molecular oxygen as environmentally benign oxidants. In this manuscript, we illustrate developments achieved in this area to access chiral epoxides, sulfoxides, γ-lactones, α-hydroxylated carbonyl compounds, and derivatives thereof.

    2. Advances and Applications in Organocatalytic Asymmetric aza-Michael Addition (pages 917–925)

      Prof. Dr. Jun Wang, Prof. Dr. Pengfei Li, Pui Ying Choy, Prof. Dr. Albert S. C. Chan and Prof. Dr. Fuk Yee Kwong

      Article first published online: 29 MAY 2012 | DOI: 10.1002/cctc.201200135

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      Go forth and make bonds: The aza-Michael addition is an excellent way of forming C[BOND]N bonds and is of tremendous significance in asymmetric synthesis. Recently, impressive progress has been achieved by employing new nitrogen nucleophiles, suitable acceptors, and more efficient catalyst systems for this important transformation. This review surveys the advances among intermolecular- and intramolecular aza-Michael addition and domino reactions involved aza-Michael addition developed between 2010 and early 2012.

    3. H-Donor Anion Acceptor Organocatalysis—The Ionic Electrophile Activation Approach (pages 926–936)

      Stephan Beckendorf, Sören Asmus and Dr. Olga García Mancheño

      Article first published online: 6 JUN 2012 | DOI: 10.1002/cctc.201200134

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      Loving getting in touch: The use of the high affinity of certain small organic molecules to anions for the development of acceptor catalysis is discussed. Covered in particular, are reactions that imply the activation of ionic electrophiles by H-bonding to their counter anions.

    4. Oxidative N-Heterocyclic Carbene Catalysis (pages 937–941)

      Dr. Christiane E. I. Knappke, Adrian Imami and Prof. Dr. Axel Jacobi von Wangelin

      Article first published online: 23 MAY 2012 | DOI: 10.1002/cctc.201200133

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      Hand-in-hand with oxidants: Highlighted are the developments in oxidative (and oxygenative) N-heterocyclic carbene-catalyzed acylation reactions that employ external oxidants.

    5. Organocatalytic Enantioselective α-Alkylation of Aldehydes (pages 942–953)

      Dr. Jan Vesely and Prof. Dr. Ramon Rios

      Article first published online: 13 MAR 2012 | DOI: 10.1002/cctc.201200072

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      The knights that say enamine: Organocatalytic intermolecular α-alkylation has been a long awaited prize for organocatalytic chemists. Recently several research groups have reported several methodologies with high levels of stereoselectivity. In this Minireview we aim to describe the efforts made in this field in recent years.

  7. Highlight

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Asymmetric Organocatalysis Meets Hypervalent Iodine Chemistry for the α-Functionalization of Carbonyl Compounds (pages 955–958)

      Dr. Davinia Fernández González, Dr. Fides Benfatti and Prof. Dr. Jérôme Waser

      Article first published online: 29 MAY 2012 | DOI: 10.1002/cctc.201200116

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      A hype around organocatalysis: Organocatalysis and hypervalent iodine(III) chemistry are receiving increasing attention in research. A fusion of the two gives rise to interesting synthetic possibilities that benefit from the advantages of both areas. Selected examples combining asymmetric organocatalytic processes and hypervalent iodine reagents for the functionalization of carbonyl compounds are discussed here.

  8. Communications

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Organocatalytic 1,4-Addition Reaction of α,β-γ,δ-Diunsaturated Aldehydes versus 1,6-Addition Reaction (pages 959–962)

      Prof. Dr. Yujiro Hayashi, Daichi Okamura, Shigenobu Umemiya and Dr. Tadafumi Uchimaru

      Article first published online: 29 MAY 2012 | DOI: 10.1002/cctc.201200161

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      Michael addition for the win: The 1,4-addition reaction is reported to be the main reaction mode in the Michael reaction of α,β-γ,δ-diunsaturated aldehydes. Several nucleophiles were catalyzed by diphenylprolinol silyl ether, which affords the Michael product with excellent enantioselectivity. Selectivity between 1,4- versus 1,6-addition reaction was investigated by ab initio calculations, and reveals that 1,4-addition is preferable.

    2. Guanidine/Azole Binary System as an Efficient Catalyst for Morita–Baylis–Hillman Reaction (pages 963–967)

      Prof. Dr. Masahiro Terada, Satoko Fukuchi, Kei Amagai, Dr. Megumi Nakano and Dr. Hitoshi Ube

      Article first published online: 8 JUN 2012 | DOI: 10.1002/cctc.201200149

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      A catalyst is more than ones and zeros: The efficient catalysis for the Morita–Baylis–Hillman reaction of aromatic aldehydes with cyclic enones was demonstrated using a binary catalytic system consisting of a guanidine derivative and an azole derivative. The present binary system is well embedded into the catalytic cycles to stabilize the anionic intermediates through the hydrogen-bonding interaction with the guanidinium ion.

    3. Organocatalytic Stereoselective α-Formylation of Ketones (pages 968–971)

      Montse Guiteras Capdevila, Dr. Enrico Emer, Dr. Andrea Gualandi, Diego Petruzziello, Dr. Stefano Grilli and Prof. Pier Giorgio Cozzi

      Article first published online: 21 MAY 2012 | DOI: 10.1002/cctc.201200122

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      A formal… formyl: N-Methylbenzothiazolium iodide, a precursor of carbene and an electrophilic compound, has been shown to reacts with the enamine of ketones in a highly enantioselective formylation reaction.

    4. Immobilization of Chiral Bifunctional Organocatalysts on Poly(methylhydrosiloxane) (pages 972–975)

      Dr. Alessandra Puglisi, Prof. Maurizio Benaglia, Prof. Rita Annunziata and Prof. Jay S. Siegel

      Article first published online: 18 APR 2012 | DOI: 10.1002/cctc.201200114

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      Takemoto promotes: Enantiomerically pure bifunctional chiral catalysts are immobilized on poly(methylhydrosiloxane). A supported Takemoto-type catalyst promoted the diethyl malonate addition to nitrostyrene in fair to good yields and up to 83 % ee, and its recyclability is demonstrated.

    5. Modular Three-Component Organocatalytic Synthesis of 3,4-Disubstituted Pyrroles by a One-Pot Domino Reaction (pages 976–979)

      Cecilia Martín-Santos, Carlos Jarava-Barrera, Dr. Alejandro Parra, Francisco Esteban, Prof. Carmen Navarro-Ranninger and Dr. José Alemán

      Article first published online: 22 MAY 2012 | DOI: 10.1002/cctc.201200104

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      Pull the trigger! The use of (Z)-β,β-bromo-nitroalkenes under enamine catalysis provides the 1,4-Michael adduct intermediate, which upon treatment with the desired amine (R3NH2) triggers the domino reaction to provide the final 3,4-disubstituted pyrrole derivatives.

    6. Efficient Asymmetric Synthesis of a Bicyclic Amino Acid as a Core Structure of Telaprevir (pages 980–982)

      Dr. Seiji Shirakawa, Dr. Yan Liu, Asuka Usui and Prof. Dr. Keiji Maruoka

      Article first published online: 4 APR 2012 | DOI: 10.1002/cctc.201200081

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      Telaprevir building block: Efficient asymmetric synthesis of bicyclic amino acid as a core structure of telaprevir has been accomplished via phase-transfer catalyzed stereoselective conjugate addition of glycine derivative to cyclopent-1-enecarbaldehyde. This synthetic method can be applied to the asymmetric synthesis of 3-substituted prolines.

    7. Organocatalyzed Isomerization of α-Substituted Alkynoates into Trisubstituted Allenoates by Dynamic Kinetic Resolution (pages 983–985)

      Dr. Tsubasa Inokuma, Masaya Furukawa, Yusuke Suzuki, Dr. Tetsutaro Kimachi, Dr. Yusuke Kobayashi and Prof. Dr. Yoshiji Takemoto

      Article first published online: 14 MAR 2012 | DOI: 10.1002/cctc.201200065

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      The left hand claps the right: Highly enantioselective isomerization of racemic α-substituted alkynoates into nonracemic trisubstituted allenoates was achieved through the catalytic dynamic kinetic resolution mediated by bifunctional benzothiadiazine. This reaction proceeded with good conversion and high enantioselectivity to give the desired allenoates in good yields without recovering the significant amounts of starting materials.

  9. Full Papers

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. Catalytic Asymmetric Synthesis of Chromene Derivatives by Iminium Ion Catalysis (pages 987–992)

      Prof. Dr. Magnus Rueping, Dr. Estíbaliz Merino and Dr. Erli Sugiono

      Article first published online: 25 MAY 2012 | DOI: 10.1002/cctc.201200151

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      Cycles and cascades: A highly efficient diarylprolinol TMS ether catalyzed enantioselective addition–acetalization cascade reaction of cyclic 1,3-diketones with α,β-unsaturated aldehydes provides access to valuable hydroxychromenone derivatives. Thus, lactones, oxadecalinones, and benzopyranes can be obtained without loss of enantiomeric excess.

    2. Guanidines: Highly Nucleophilic Organocatalysts (pages 993–999)

      Biplab Maji, Dr. David S. Stephenson and Prof. Dr. Herbert Mayr

      Article first published online: 29 MAY 2012 | DOI: 10.1002/cctc.201200143

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      Which one is faster? Kinetic investigations of the reactions of guanidines with diarylcarbenium ions allow for the derivation of nucleophilicity parameters N and for comparison with other organocatalysts.

    3. A Liquid–Liquid Biphasic Homogeneous Organocatalytic Aldol Protocol Based on the Use of a Silica Gel Bound Multilayered Ionic Liquid Phase (pages 1000–1006)

      Dr. Elisa Montroni, Prof. Marco Lombardo, Dr. Arianna Quintavalla, Prof. Claudio Trombini, Prof. Michelangelo Gruttadauria and Dr. Francesco Giacalone

      Article first published online: 30 APR 2012 | DOI: 10.1002/cctc.201200125

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      Double duty: A liquid–liquid biphasic homogeneous protocol for the asymmetric aldol reaction is proposed, based on the use of a cis-ion-tagged proline dissolved in the liquid film of a multilayered ionic liquid, covalently bonded to silica gel. The resulting catalytically active material acts as a catalyst reservoir during the reaction stage and as a catalyst sponge during workup, allowing for several reuses with high cumulative productivity values up to 523.

    4. Organocatalytic Michael Reaction of Nitroenamine Derivatives with Aldehydes: Short and Efficient Asymmetric Synthesis of (−)-Oseltamivir (pages 1007–1012)

      Dr. Jiang Weng, Yong-Bo Li, Rui-Bin Wang and Prof. Dr. Gui Lu

      Article first published online: 22 MAY 2012 | DOI: 10.1002/cctc.201200124

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      Give it a nitro boost! Nitroenamine derivatives were used as a new class of Michael acceptors in the organocatalytic Michael reaction. Moreover, a highly efficient and simple synthesis of (−)-oseltamivir was accomplished in only a five-step synthesis.

    5. Organocatalyst Efficiency in the Michael Additions of Aldehydes to Nitroalkenes in Water and in a Ball-Mill (pages 1013–1018)

      Dr. Eva Veverková, Dr. Viera Poláčková, Lucia Liptáková, Eva Kázmerová, Dr. Mária Mečiarová, Prof. Dr. Štefan Toma and Dr. Radovan Šebesta

      Article first published online: 10 MAY 2012 | DOI: 10.1002/cctc.201200105

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      Having a ball: Pyrrolidine-derived organocatalysts were used in the Michael addition of aldehydes to nitroalkenes in aqueous and solvent-free conditions to afford Michael adducts in high yield, diastereoselectivity, and enantioselectivity.

  10. Preview

    1. Top of page
    2. Cover Picture
    3. Back Cover
    4. Editorial
    5. Graphical Abstract
    6. News
    7. Minireviews
    8. Highlight
    9. Communications
    10. Full Papers
    11. Preview
    1. You have free access to this content
      Preview: ChemCatChem 8/2012 (page 1019)

      Article first published online: 22 JUN 2012 | DOI: 10.1002/cctc.201290021

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