Literature DB >> 20302338

Enantioselective alkenylation via nickel-catalyzed cross-coupling with organozirconium reagents.

Sha Lou1, Gregory C Fu.   

Abstract

A new family of organometallic compounds, organozirconium reagents, are shown to serve as suitable partners in cross-coupling reactions of (activated) secondary alkyl electrophiles. Thus, the first catalytic method for coupling secondary alpha-bromoketones with alkenylmetal reagents has been developed, specifically, a mild, versatile, and stereoconvergent carbon-carbon bond-forming process that generates potentially labile beta,gamma-unsaturated ketones with good enantioselectivity.

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Year:  2010        PMID： 20302338      PMCID： PMC2860276          DOI： 10.1021/ja1017046

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


  14 in total

1.  Suzuki cross-couplings of unactivated secondary alkyl bromides and iodides.

Authors:  Jianrong Zhou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2004-02-11       Impact factor: 15.419

2.  Catalytic asymmetric Hiyama cross-couplings of racemic alpha-bromo esters.

Authors:  Xing Dai; Neil A Strotman; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-02-27       Impact factor: 15.419

3.  Domino iron catalysis: direct aryl-alkyl cross-coupling.

Authors:  Waldemar Maximilian Czaplik; Matthias Mayer; Axel Jacobi von Wangelin
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 4.  Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions.

Authors:  Alena Rudolph; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents.

Authors:  David A Powell; Toshihide Maki; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-01-19       Impact factor: 15.419

6.  Nickel/bis(oxazoline)-catalyzed asymmetric Kumada reactions of alkyl electrophiles: cross-couplings of racemic alpha-bromoketones.

Authors:  Sha Lou; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

7.  Catalytic asymmetric cross-couplings of racemic alpha-bromoketones with arylzinc reagents.

Authors:  Pamela M Lundin; Jorge Esquivias; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  Palladium- (and nickel-) catalyzed vinylation of aryl halides.

Authors:  Scott E Denmark; Christopher R Butler
Journal:  Chem Commun (Camb)       Date:  2008-08-27       Impact factor: 6.222

9.  Iron-catalyzed cross-coupling of alkyl halides with alkenyl grignard reagents.

Authors:  Amandine Guérinot; Sébastien Reymond; Janine Cossy
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

10.  Palladium-catalyzed enantioselective alpha-arylation and alpha-vinylation of oxindoles facilitated by an axially chiral P-stereogenic ligand.

Authors:  Alexander M Taylor; Ryan A Altman; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419
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  21 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.  N-Heterocyclic Carbene Bound Nickel(I) Complexes and Their Roles in Catalysis.

Authors:  Kainan Zhang; Martin Conda-Sheridan; Shayna Cooke; Janis Louie
Journal:  Organometallics       Date:  2011-05-09       Impact factor: 3.876

3.  Enantioselective α-vinylation of aldehydes via the synergistic combination of copper and amine catalysis.

Authors:  Eduardas Skucas; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2012-05-29       Impact factor: 15.419

4.  Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

Authors:  Jason M Stevens; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-08-05       Impact factor: 15.419

5.  Asymmetric transition metal-catalyzed cross-coupling reactions for the construction of tertiary stereocenters.

Authors:  Elizabeth C Swift; Elizabeth R Jarvo
Journal:  Tetrahedron       Date:  2013-07-22       Impact factor: 2.457

6.  Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins.

Authors:  Nathan A Owston; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-09-01       Impact factor: 15.419

7.  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

8.  Catalytic enantioselective cross-couplings of secondary alkyl electrophiles with secondary alkylmetal nucleophiles: Negishi reactions of racemic benzylic bromides with achiral alkylzinc reagents.

Authors:  Jörg T Binder; Christopher J Cordier; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-10-05       Impact factor: 15.419

9.  A Catalytic Intermolecular Formal Ene Reaction between Ketone-Derived Silyl Enol Ethers and Alkynes.

Authors:  Stephen D Holmbo; Nicole A Godfrey; Joshua J Hirner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2016-09-16       Impact factor: 15.419

10.  Pd-catalyzed cross-coupling of potassium alkenyltrifluoroborates with 2-chloroacetates and 2-chloroacetamides.

Authors:  Gary A Molander; Thiago Barcellos; Kaitlin M Traister
Journal:  Org Lett       Date:  2013-06-14       Impact factor: 6.005
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