Literature DB >> 21797265

Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters.

Yi-Ming Wang1, Christian N Kuzniewski, Vivek Rauniyar, Christina Hoong, F Dean Toste.   

Abstract

A highly enantioselective transformation catalyzed by chiral (acyclic diaminocarbene)gold(I) complexes is reported. The enantioselective synthesis of 2-substituted chromenyl pivalates from racemic phenol-substituted propargyl pivalates was developed. Rearrangement of the substrates in the presence of cationic gold gave allene intermediates, whose cyclization resulted in formation of enantioenriched product through a dynamic kinetic asymmetric transformation.

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Year:  2011        PMID： 21797265      PMCID： PMC3650467          DOI： 10.1021/ja205068j

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


  36 in total

1.  Gold(I)-catalyzed enantioselective synthesis of functionalized indenes.

Authors:  Alberto Martínez; Patricia García-García; Manuel A Fernández-Rodríguez; Félix Rodríguez; Roberto Sanz
Journal:  Angew Chem Int Ed Engl       Date:  2010-06-21       Impact factor: 15.336

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

Review 3.  Gold and platinum catalysis--a convenient tool for generating molecular complexity.

Authors:  Alois Fürstner
Journal:  Chem Soc Rev       Date:  2009-07-22       Impact factor: 54.564

4.  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

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

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

6.  Gold-catalyzed decorations of arenes and heteroarenes with C-C multiple bonds.

Authors:  Marco Bandini
Journal:  Chem Soc Rev       Date:  2010-11-22       Impact factor: 54.564

7.  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

8.  Gold-catalyzed [4C+2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: mechanistic aspects of the divergence between [4C+3C] and [4C+2C] pathways.

Authors:  Isaac Alonso; Beatriz Trillo; Fernando López; Sergi Montserrat; Gregori Ujaque; Luis Castedo; Agustí Lledós; Jose L Mascareñas
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

9.  Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.

Authors:  Florian Kleinbeck; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-07-08       Impact factor: 15.419

10.  Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis.

Authors:  Lian-Jun Liu; Feijun Wang; Wenfeng Wang; Mei-Xin Zhao; Min Shi
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883
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  22 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  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

3.  Enantioselective cyclizations of silyloxyenynes catalyzed by cationic metal phosphine complexes.

Authors:  Jean-François Brazeau; Suyan Zhang; Ignacio Colomer; Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2012-01-31       Impact factor: 15.419

4.  Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Authors:  Weiwei Zi; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-08-19       Impact factor: 15.419

Review 5.  Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors:  Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal:  Chem Soc Rev       Date:  2012-12-07       Impact factor: 54.564

6.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

Review 7.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

8.  Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Authors:  Dimitri A Khrakovsky; Chuanzhou Tao; Miles W Johnson; Richard T Thornbury; Sophia L Shevick; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-20       Impact factor: 15.336

9.  Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization.

Authors:  Zachary L Niemeyer; Suresh Pindi; Dimitri A Khrakovsky; Christian N Kuzniewski; Cynthia M Hong; Leo A Joyce; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

10.  Enantioselective Synthesis of Trisubstituted Allenyl-B(pin) Compounds by Phosphine-Cu-Catalyzed 1,3-Enyne Hydroboration. Insights Regarding Stereochemical Integrity of Cu-Allenyl Intermediates.

Authors:  Youming Huang; Juan Del Pozo; Sebastian Torker; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2018-02-08       Impact factor: 15.419
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