Literature DB >> 27276235

Nickel-Catalyzed Asymmetric Kumada Cross-Coupling of Symmetric Cyclic Sulfates.

Meredith S Eno1, Alexander Lu1, James P Morken1.   

Abstract

Nickel-catalyzed enantioselective cross-couplings between symmetric cyclic sulfates and aromatic Grignard reagents are described. These reactions are effective with a broad range of substituted cyclic sulfates and deliver products with asymmetric tertiary carbon centers. Mechanistic experiments point to a stereoinvertive SN2-like oxidative addition of a nickel complex to the electrophilic substrate.

Entities:  

Year:  2016        PMID： 27276235      PMCID： PMC5539537          DOI： 10.1021/jacs.6b03384

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


  58 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.  Synthesis and reactivity of new chiral bicyclic phospholanes as acyl-transfer catalysts.

Authors:  James A MacKay; Edwin Vedejs
Journal:  J Org Chem       Date:  2006-01-20       Impact factor: 4.354

3.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

4.  A concise synthesis of eupomatilones 4, 6, and 7 by rhodium-catalyzed enantioselective desymmetrization of cyclic meso anhydrides with organozinc reagents generated in situ.

Authors:  Jeffrey B Johnson; Eric A Bercot; Catherine M Williams; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Ni-catalyzed cascade formation of C(sp3)--C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides.

Authors:  Vilas B Phapale; Elena Buñuel; Miguel García-Iglesias; Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

6.  Nickel complexes of a pincer amidobis(amine) ligand: synthesis, structure, and activity in stoichiometric and catalytic C-C bond-forming reactions of alkyl halides.

Authors:  Oleg Vechorkin; Zsolt Csok; Rosario Scopelliti; Xile Hu
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

7.  Copper-catalyzed alkyl-alkyl cross-coupling reactions using hydrocarbon additives: efficiency of catalyst and roles of additives.

Authors:  Takanori Iwasaki; Reiko Imanishi; Ryohei Shimizu; Hitoshi Kuniyasu; Jun Terao; Nobuaki Kambe
Journal:  J Org Chem       Date:  2014-07-10       Impact factor: 4.354

8.  Nickel/bis(oxazoline)-catalyzed asymmetric Negishi arylations of racemic secondary benzylic electrophiles to generate enantioenriched 1,1-diarylalkanes.

Authors:  Hien-Quang Do; E R R Chandrashekar; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2013-10-28       Impact factor: 15.419

9.  Traceless directing group for stereospecific nickel-catalyzed alkyl-alkyl cross-coupling reactions.

Authors:  Margaret A Greene; Ivelina M Yonova; Florence J Williams; Elizabeth R Jarvo
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005

10.  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
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  5 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

3.  Conformational Flexibility as a Tool for Enabling Site-Selective Functionalization of Unactivated sp3 C-O Bonds in Cyclic Acetals.

Authors:  Ciro Romano; Laura Talavera; Enrique Gómez-Bengoa; Ruben Martin
Journal:  J Am Chem Soc       Date:  2022-06-24       Impact factor: 16.383

4.  Transition-metal-free regioselective C-H halogenation of imidazo[1,2-a]pyridines: sodium chlorite/bromite as the halogen source.

Authors:  Junxuan Li; Jiayi Tang; Yuanheng Wu; Qiuxing He; Yue Yu
Journal:  RSC Adv       Date:  2018-02-01       Impact factor: 4.036

5.  DFT insight into asymmetric alkyl-alkyl bond formation via nickel-catalysed enantioconvergent reductive coupling of racemic electrophiles with olefins.

Authors:  Chao-Shen Zhang; Bei-Bei Zhang; Liang Zhong; Xiang-Yu Chen; Zhi-Xiang Wang
Journal:  Chem Sci       Date:  2022-02-25       Impact factor: 9.825
  5 in total

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