Literature DB >> 23843307

Nickel-catalyzed enantioselective arylation of pyridinium ions: harnessing an iminium ion activation mode.

Stephen T Chau1, J Patrick Lutz, Kevin Wu, Abigail G Doyle.   

Abstract

Entities:  

Keywords:  Negishi reaction; asymmetric catalysis; cross-coupling; nickel; nitrogen heterocycles

Mesh：

Substances：

Year:  2013        PMID： 23843307      PMCID： PMC4811189          DOI： 10.1002/anie.201303994

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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  22 in total

1.  A diastereoselective synthesis of 2,4-disubstituted piperidines: scaffolds for drug discovery.

Authors:  P S Watson; B Jiang; B Scott
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

2.  Unusually lower barrier to reductive elimination in an 18-electron .eta.3-allyl(organo)nickel(II) complex than those for the 16-electron .eta.3-allyl counterpart and its 16-electron .eta.1-allyl isomer.

Authors:  H Kurosawa; H Ohnishi; M Emoto; Y Kawasaki; S Murai
Journal:  J Am Chem Soc       Date:  1988-08-01       Impact factor: 15.419

3.  Phosphoramidites: privileged ligands in asymmetric catalysis.

Authors:  Johannes F Teichert; Ben L Feringa
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-29       Impact factor: 15.336

4.  Copper-catalyzed coupling of pyridines and quinolines with alkynes: a one-step, asymmetric route to functionalized heterocycles.

Authors:  Daniel A Black; Ramsay E Beveridge; Bruce A Arndtsen
Journal:  J Org Chem       Date:  2008-01-24       Impact factor: 4.354

5.  (R)-3-METHYL-3-PHENYL-1-PENTENE VIA CATALYTIC ASYMMETRIC HYDROVINYLATION.

Authors:  Craig R Smith; Aibin Zhang; Daniel J Mans; T V Rajanbabu; Scott E Denmark; Min Xie
Journal:  Organic Synth       Date:  2008

6.  Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.

Authors:  Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2012-03-02       Impact factor: 6.005

7.  Generation of N-acylpyridinium ions from pivaloyl chloride and pyridine derivatives by means of silyl triflates

Authors: 
Journal:  J Org Chem       Date:  2000-12-29       Impact factor: 4.354

8.  Amidocarbonylation-An Efficient Route to Amino Acid Derivatives.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-03       Impact factor: 15.336

9.  Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.

Authors:  Kevin T Sylvester; Kevin Wu; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

10.  Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines.

Authors:  Claude Legault; André B Charette
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419
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  12 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Authors:  Simon Duttwyler; Shuming Chen; Colin Lu; Brandon Q Mercado; Robert G Bergman; Jonathan A Ellman
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-06       Impact factor: 15.336

3.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

4.  Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.

Authors:  Benedikt Wanner; Imants Kreituss; Osvaldo Gutierrez; Marisa C Kozlowski; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2015-08-26       Impact factor: 15.419

5.  Enantioselective, nickel-catalyzed Suzuki cross-coupling of quinolinium ions.

Authors:  Jason D Shields; Derek T Ahneman; Thomas J A Graham; Abigail G Doyle
Journal:  Org Lett       Date:  2013-11-26       Impact factor: 6.005

6.  Nickel-catalyzed enantioselective arylation of pyridine.

Authors:  J Patrick Lutz; Stephen T Chau; Abigail G Doyle
Journal:  Chem Sci       Date:  2016-03-08       Impact factor: 9.825

7.  Nickel-Catalyzed C-3 Direct Arylation of Pyridinium Ions for the Synthesis of 1-Azafluorenes.

Authors:  Jean-Nicolas Desrosiers; Xudong Wei; Osvaldo Gutierrez; Jolaine Savoie; Bo Qu; Xingzhong Zeng; Heewon Lee; Nelu Grinberg; Nizar Haddad; Nathan K Yee; Frank Roschangar; Jinhua J Song; Marisa C Kozlowski; Chris H Senanayake
Journal:  Chem Sci       Date:  2016-05-19       Impact factor: 9.825

8.  Enantioselective Catalytic Dearomative Addition of Grignard Reagents to 4-Methoxypyridinium Ions.

Authors:  Yafei Guo; Marta Castiñeira Reis; Johanan Kootstra; Syuzanna R Harutyunyan
Journal:  ACS Catal       Date:  2021-06-28       Impact factor: 13.084

9.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354

Review 10.  Convergent Synthesis of Diverse Tetrahydropyridines via Rh(I)-Catalyzed C-H Functionalization Sequences.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317
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