Literature DB >> 28074655

Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Faben A Cruz1, Vy M Dong1.   

Abstract

We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high enantio-, diastereo-, and regioselectivity. Our study highlights the power of catalysis to activate two common functional groups and provide access to divergent stereoisomers and constitutional structures.

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Year:  2017        PMID： 28074655      PMCID： PMC9141309          DOI： 10.1021/jacs.6b10680

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  51 in total

1.  Transition metal catalyzed alkene and alkyne hydroacylation.

Authors:  Michael C Willis
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

2.  Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis.

Authors:  Simon Krautwald; Michael A Schafroth; David Sarlah; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2014-02-13       Impact factor: 15.419

3.  N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes.

Authors:  Akkattu T Biju; Nathalie E Wurz; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

4.  Stereodivergent Dual Catalytic α-Allylation of Protected α-Amino- and α-Hydroxyacetaldehydes.

Authors:  Tobias Sandmeier; Simon Krautwald; Hannes F Zipfel; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-02       Impact factor: 15.336

5.  Regioselective Rhodium-Catalyzed Addition of 1,3-Dicarbonyl Compounds to Terminal Alkynes.

Authors:  Thorsten M Beck; Bernhard Breit
Journal:  Org Lett       Date:  2015-12-18       Impact factor: 6.005

6.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

7.  An Ir/Zn Dual Catalysis for Enantio- and Diastereodivergent α-Allylation of α-Hydroxyketones.

Authors:  Xiaohong Huo; Rui He; Xiao Zhang; Wanbin Zhang
Journal:  J Am Chem Soc       Date:  2016-08-25       Impact factor: 15.419

8.  Cooperative Palladium/Proline-Catalyzed Direct α-Allylic Alkylation of Ketones with Alkynes.

Authors:  Chi Yang; Kaifan Zhang; Zijun Wu; Hequan Yao; Aijun Lin
Journal:  Org Lett       Date:  2016-09-29       Impact factor: 6.005

9.  Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: merging organic and transition metal catalysis.

Authors:  Bradley G Jellerichs; Jong-Rock Kong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2003-07-02       Impact factor: 15.419

10.  Copper-catalysed enantioselective stereodivergent synthesis of amino alcohols.

Authors:  Shi-Liang Shi; Zackary L Wong; Stephen L Buchwald
Journal:  Nature       Date:  2016-03-28       Impact factor: 49.962
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  28 in total

1.  Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Authors:  Xiao-Hui Yang; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-08-09       Impact factor: 15.419

2.  Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Authors:  Chibueze I Onyeagusi; Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2020-02-04       Impact factor: 6.005

3.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

4.  Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles.

Authors:  Nathan J Adamson; Katherine C E Wilbur; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-02-20       Impact factor: 15.419

5.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

Review 6.  Alkynes as Electrophilic or Nucleophilic Allylmetal Precursors in Transition-Metal Catalysis.

Authors:  Alexander M Haydl; Bernhard Breit; Tao Liang; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-10       Impact factor: 15.336

7.  Rhodium-Catalyzed Hydrofunctionalization: Enantioselective Coupling of Indolines and 1,3-Dienes.

Authors:  Xiao-Hui Yang; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-27       Impact factor: 15.419

8.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

9.  Divergent Control of Point and Axial Stereogenicity: Catalytic Enantioselective C-N Bond-Forming Cross-Coupling and Catalyst-Controlled Atroposelective Cyclodehydration.

Authors:  Yongseok Kwon; Alex J Chinn; Byoungmoo Kim; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-23       Impact factor: 15.336

10.  Enantioselective Addition of α-Nitroesters to Alkynes.

Authors:  Ryan T Davison; Patrick D Parker; Xintong Hou; Crystal P Chung; Sara A Augustine; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-07       Impact factor: 15.336
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