Advanced Synthesis & Catalysis

Cover image for Vol. 353 Issue 1

January 10, 2011

Volume 353, Issue 1

Pages 1–169

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Commentary
    5. Communications
    6. Full Papers
    1. Cover Picture: (Adv. Synth. Catal. 1/2011) (page 1)

      Version of Record online: 20 JAN 2011 | DOI: 10.1002/adsc.201190000

      Thumbnail image of graphical abstract

      The cover picture, provided by Fandrick, Fandrick, and Senanayake, depicts the copper-catalyzed asymmetric propargylation of aldehydes. The process is based on a copper alkoxide-promoted B/Cu exchange to generate an allenyl copper intermediate. The process is initiated by ligand exchange of the ligated copper(II) isobutyrate complex with lithium tert-butoxide, wherein the resulting copper alkoxide complex undergoes an exchange with the propargyl borolane reagent to generate the key allenyl copper intermediate. After propargylation of an aldehyde, the resulting homopropargylic alkoxide copper complex readily participates in another B/Cu exchange to complete the catalytic cycle. Employing the MeOBIBOP ligand allows for exceptional control of both enantioselectivity and site selectivity for the homopropargylic alcohol. This two-step process, wherein the product of the alkylation readily reacts with a stoichiometric reagent to regenerate the active nucleophile provides an operationally simple process to effect the propargylation of aldehydes with broad functional group tolerance.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Commentary
    5. Communications
    6. Full Papers
  3. Commentary

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Commentary
    5. Communications
    6. Full Papers
  4. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Commentary
    5. Communications
    6. Full Papers
    1. Base-Mediated Tandem Reaction Consisting of an Acyl Shift Strategy Leading to 4,5-Disubstiuted Furan-2(5H)-ones (pages 31–35)

      Yong Lei, Zhi-Qiang Wang, Ye-Xiang Xie, Shang-Ci Yu, Bo-Xiao Tang and Jin-Heng Li

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/adsc.201000762

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    2. One-Pot Synthesis of Triazolothiadiazepine 1,1-Dioxide Derivatives via Copper-Catalyzed Tandem [3+2] Cycloaddition/N-Arylation (pages 41–48)

      Deepak Kumar Barange, Yu-Chen Tu, Veerababurao Kavala, Chun-Wei Kuo and Ching-Fa Yao

      Version of Record online: 4 JAN 2011 | DOI: 10.1002/adsc.201000465

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    3. An Efficient Catalytic Chromium-Mediated Iodocyclopropanation Reaction: Stereoselective Synthesis of Iodocyclopropanecarboxamides (pages 49–52)

      José M. Concellón, Humberto Rodríguez-Solla, Elena G. Blanco, Santiago García-Granda and and M. Rosario Díaz

      Version of Record online: 30 DEC 2010 | DOI: 10.1002/adsc.201000574

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    4. Titanium/Palladium-Mediated Regioselective Propargylation of Ketones using Propargylic Carbonates as Pronucleophiles (pages 73–78)

      Alba Millán, Luis Álvarez de Cienfuegos, Ana Martín-Lasanta, Araceli G. Campaña and Juan M. Cuerva

      Version of Record online: 22 DEC 2010 | DOI: 10.1002/adsc.201000655

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    5. Synthesis of 2,4- and 2,5-Disubstituted Oxazoles via Metal- Catalyzed Cross-Coupling Reactions (pages 79–83)

      Carla M. Counceller, Chad C. Eichman, Nicolas Proust and James P. Stambuli

      Version of Record online: 30 DEC 2010 | DOI: 10.1002/adsc.201000668

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  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Commentary
    5. Communications
    6. Full Papers
    1. Redesign of the Phosphate Binding Site of L-Rhamnulose- 1-Phosphate Aldolase towards a Dihydroxyacetone Dependent Aldolase (pages 89–99)

      Xavier Garrabou, Jesús Joglar, Teodor Parella, Ramon Crehuet, Jordi Bujons and Pere Clapés

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/adsc.201000719

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    2. Magnetite (Fe3O4) Nanoparticles-Catalyzed Sonogashira– Hagihara Reactions in Ethylene Glycol under Ligand-Free Conditions (pages 125–132)

      Habib Firouzabadi, Nasser Iranpoor, Mohammad Gholinejad and Jafar Hoseini

      Version of Record online: 30 DEC 2010 | DOI: 10.1002/adsc.201000390

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    3. Effective Guanidine-Catalyzed Synthesis of Carbonate and Carbamate Derivatives from Propargyl Alcohols in Supercritical Carbon Dioxide (pages 133–146)

      Nicola Della Ca', Bartolo Gabriele, Giuseppe Ruffolo, Lucia Veltri, Tito Zanetta and Mirco Costa

      Version of Record online: 20 JAN 2011 | DOI: 10.1002/adsc.201000607

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    4. Hydroperoxidation of Tertiary Alkylaromatics Catalyzed By N-Hydroxyphthalimide and Aldehydes under Mild Conditions (pages 147–154)

      Lucio Melone, Cristian Gambarotti, Simona Prosperini, Nadia Pastori, Francesco Recupero and Carlo Punta

      Version of Record online: 18 JAN 2011 | DOI: 10.1002/adsc.201000786

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