Literature DB >> 21449537

Mobilizing Cu(I) for carbon-carbon bond forming catalysis in the presence of thiolate. Chemical mimicking of metallothioneins.

Zhihui Zhang1, Matthew G Lindale, Lanny S Liebeskind.   

Abstract

<pan class="Chemical">span class="Chemical">Copperpan>(I) is rendered catalytically viable in the presence of <sppan>an class="Chemical">thiolate by the design of a small mole<span class="Chemical">cule chemical analogue of the metallothionein system in which an N-O reactant serves the same conceptual purpose of the S-S reactant of the biological system.

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Year:  2011        PMID: 21449537      PMCID: PMC3128984          DOI: 10.1021/ja200792m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  37 in total

Review 1.  Metallothionein: the multipurpose protein.

Authors:  P Coyle; J C Philcox; L C Carey; A M Rofe
Journal:  Cell Mol Life Sci       Date:  2002-04       Impact factor: 9.261

Review 2.  Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Authors:  Gwilherm Evano; Nicolas Blanchard; Mathieu Toumi
Journal:  Chem Rev       Date:  2008-08       Impact factor: 60.622

3.  Palladium-catalyzed coupling of thiol esters with aryl and primary and secondary alkyl organoindium reagents.

Authors:  Bryan W Fausett; Lanny S Liebeskind
Journal:  J Org Chem       Date:  2005-06-10       Impact factor: 4.354

4.  Substituted alkyne synthesis under nonbasic conditions: copper carboxylate-mediated, palladium-catalyzed thioalkyne-boronic acid cross-coupling.

Authors:  C Savarin; J Srogl; L S Liebeskind
Journal:  Org Lett       Date:  2001-01-11       Impact factor: 6.005

5.  Copper-release from yeast Cu(I)-metallothionein by nitric oxide (NO).

Authors:  H J Hartmann; U Weser
Journal:  Biometals       Date:  2000-06       Impact factor: 2.949

6.  On the Mechanism of Pd(0)-Catalyzed, Cu(I) Carboxylate-Mediated Thioorganic-Boronic Acid Desulfitative Coupling. A Non-innocent Role for Carboxylate Ligand.

Authors:  Djamaladdin G Musaev; Lanny S Liebeskind
Journal:  Organometallics       Date:  2009-07-22       Impact factor: 3.876

7.  A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic s-acylthiosalicylamides in air at room temperature.

Authors:  Lanny S Liebeskind; Hao Yang; Hao Li
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether.

Authors:  France-Aimée Alphonse; Franck Suzenet; Anne Keromnes; Bruno Lebret; Gérald Guillaumet
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

9.  Synthesis of high enantiopurity N-protected alpha-amino ketones by thiol ester-organostannane cross-coupling using pH-neutral conditions.

Authors:  Hao Li; Hao Yang; Lanny S Liebeskind
Journal:  Org Lett       Date:  2008-08-30       Impact factor: 6.005

10.  A concise and scalable synthesis of high enantiopurity (-)-D-erythro-sphingosine using peptidyl thiol ester-boronic acid cross-coupling.

Authors:  Hao Yang; Lanny S Liebeskind
Journal:  Org Lett       Date:  2007-07-04       Impact factor: 6.005

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  4 in total

1.  Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.

Authors:  Hao Li; Anyu He; John R Falck; Lanny S Liebeskind
Journal:  Org Lett       Date:  2011-06-15       Impact factor: 6.005

2.  Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.

Authors:  Alexander C Wotal; Daniel J Weix
Journal:  Org Lett       Date:  2012-02-23       Impact factor: 6.005

3.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

4.  Nickel-Catalyzed Synthesis of Ketones from Alkyl Halides and Acid Chlorides: Preparation of Ethyl 4-Oxododecanoate.

Authors:  Alexander C Wotal; Donald C Batesky; Daniel J Weix
Journal:  Organic Synth       Date:  2016-02-22
  4 in total

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