Literature DB >> 11929227

Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones.

Dirk J Spielvogel1, Stephen L Buchwald.   

Abstract

A Ni(0)-BINAP system is utilized for the highly enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones with aryl chlorides and bromides. alpha-Quaternization is achieved in moderate to excellent yields. Furthermore, the rate accelerating effect caused by the addition of Zn(II) salts is investigated.

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Year:  2002        PMID： 11929227     DOI： 10.1021/ja017545t

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


  19 in total

1.  Asymmetric palladium-catalyzed intramolecular alpha-arylation of aldehydes.

Authors:  Jorge García-Fortanet; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes: effect of halide on selectivity, oxidation state, and room-temperature reactions.

Authors:  Shaozhong Ge; John F Hartwig
Journal:  J Am Chem Soc       Date:  2011-09-27       Impact factor: 15.419

3.  Enantioselective construction of all-carbon quaternary centers by branch-selective Pd-catalyzed allyl-allyl cross-coupling.

Authors:  Ping Zhang; Hai Le; Robert E Kyne; James P Morken
Journal:  J Am Chem Soc       Date:  2011-06-07       Impact factor: 15.419

4.  Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.

Authors:  James A Birrell; Jean-Nicolas Desrosiers; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-08-10       Impact factor: 15.419

5.  Design, Synthesis, and Optimization of Balanced Dual NK1/NK3 Receptor Antagonists.

Authors:  Stephen Hanessian; Thomas Jennequin; Nicolas Boyer; Vincent Babonneau; Udaykumar Soma; Clotilde Mannoury la Cour; Mark J Millan; Guillaume De Nanteuil
Journal:  ACS Med Chem Lett       Date:  2014-02-13       Impact factor: 4.345

6.  Synthesis of 5,5-disubstituted butenolides based on a Pd-catalyzed gamma-arylation strategy.

Authors:  Alan M Hyde; Stephen L Buchwald
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

7.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

8.  Enantioselective alpha-arylation of ketones with aryl triflates catalyzed by difluorphos complexes of palladium and nickel.

Authors:  Xuebin Liao; Zhiqiang Weng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2007-12-13       Impact factor: 15.419

9.  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

10.  Palladium-catalyzed α-arylation of zinc enolates of esters: reaction conditions and substrate scope.

Authors:  Takuo Hama; Shaozhong Ge; John F Hartwig
Journal:  J Org Chem       Date:  2013-08-21       Impact factor: 4.354
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