Literature DB >> 21135915

A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Nathan D Shapiro1, F Dean Toste.   

Abstract

Approaches to research in organic chemistry are as numerous as the reactions they describe. In this account, we describe our reactivity-based approach. Using our work in the area of gold-catalysis as a background, we discuss how a focus on reaction mechanism and reactivity paradigms can lead to the rapid discovery of new synthetic tools.

Entities:  

Year:  2010        PMID： 21135915      PMCID： PMC2996726          DOI： 10.1055/s-0029-1219369

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  138 in total

1.  A catalytic asymmetric Wagner-Meerwein shift.

Authors:  B M Trost; T Yasukata
Journal:  J Am Chem Soc       Date:  2001-07-25       Impact factor: 15.419

2.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

3.  Hydrogen-bonding asymmetric metal catalysis with alpha-amino acids: a simple and tunable approach to high enantioinduction.

Authors:  Yingdong Lu; Tim C Johnstone; Bruce A Arndtsen
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

4.  Ni(II)-catalyzed Conia-ene reaction of 1,3-dicarbonyl compounds with alkynes.

Authors:  Qiang Gao; Bao-Fu Zheng; Jin-Heng Li; Dan Yang
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

5.  Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects.

Authors:  A Stephen K Hashmi; Jan P Weyrauch; Wolfgang Frey; Jan W Bats
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

6.  Gold(I)-catalyzed enantioselective synthesis of pyrazolidines, isoxazolidines, and tetrahydrooxazines.

Authors:  R L Lalonde; Z J Wang; M Mba; A D Lackner; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

7.  PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Authors:  Youssef Harrak; Christophe Blaszykowski; Matthieu Bernard; Kevin Cariou; Emily Mainetti; Virginie Mouriès; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  J Am Chem Soc       Date:  2004-07-21       Impact factor: 15.419

Review 8.  Function-oriented synthesis, step economy, and drug design.

Authors:  Paul A Wender; Vishal A Verma; Thomas J Paxton; Thomas H Pillow
Journal:  Acc Chem Res       Date:  2007-12-27       Impact factor: 22.384

9.  Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations.

Authors:  Le-Ping Liu; Bo Xu; Mark S Mashuta; Gerald B Hammond
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

10.  Searching for new reactivity (Nobel lecture).

Authors:  K Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336
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  65 in total

1.  C-C coupling reactivity of an alkylgold(III) fluoride complex with arylboronic acids.

Authors:  Neal P Mankad; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

2.  Synthesis of flinderoles B and C by a gold-catalyzed allene hydroarylation().

Authors:  Rachel M Zeldin; F Dean Toste
Journal:  Chem Sci       Date:  2011-06-24       Impact factor: 9.825

3.  Gold(I)-catalyzed enantioselective [3+2] and [3+3] cycloaddition reactions of propargyl acetals/ketals.

Authors:  Cristina Navarro; Nathan D Shapiro; Maurizio Bernasconi; Takahiro Horibe; F Dean Toste
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

4.  Application of fundamental organometallic chemistry to the development of a gold-catalyzed synthesis of sulfinate derivatives.

Authors:  Miles W Johnson; Scott W Bagley; Neal P Mankad; Robert G Bergman; Vincent Mascitti; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-20       Impact factor: 15.336

5.  Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Osamu Kanno; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

6.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

Review 7.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

8.  The progression of chiral anions from concepts to applications in asymmetric catalysis.

Authors:  Robert J Phipps; Gregory L Hamilton; F Dean Toste
Journal:  Nat Chem       Date:  2012-07-24       Impact factor: 24.427

9.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

10.  Enantioselective cyclization of enamide-ynes and application to the synthesis of the kopsifoline core.

Authors:  Britton K Corkey; Stephen T Heller; Yi-Ming Wang; F Dean Toste
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457
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