Literature DB >> 18338891

Asymmetric Ni-catalyzed conjugate allylation of activated enones.

Joshua D Sieber1, James P Morken.   

Abstract

The nickel-catalyzed enantioselective addition of allylboronic acid pinacol ester, allylB(pin), is described. This reaction is highly effective with dialkylidene ketones and favors the allylation of the benzylidene site in nonsymmetric substrates. The reaction appears to proceed by conversion of the dialkylidene ketone substrate to an unsaturated pi-allyl complex (I), followed by reductive elimination. Enantioselectivities range from 91 to 94% ee for a range of substrates when chiral ligand 14 is employed.

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Year:  2008        PMID： 18338891      PMCID： PMC3065355          DOI： 10.1021/ja710922h

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


  14 in total

1.  The catalytic Sakurai reaction.

Authors:  P H Lee; K Lee; S Sung; S Chang
Journal:  J Org Chem       Date:  2001-12-14       Impact factor: 4.354

2.  Catalytic conjugate addition of allyl groups to styryl-activated enones.

Authors:  Joshua D Sieber; Shubin Liu; James P Morken
Journal:  J Am Chem Soc       Date:  2007-02-01       Impact factor: 15.419

3.  Formation of nickeladihydropyran by oxidative addition of cyclopropyl ketone. Key intermediate in nickel-catalyzed cycloaddition.

Authors:  Sensuke Ogoshi; Midue Nagata; Hideo Kurosawa
Journal:  J Am Chem Soc       Date:  2006-04-26       Impact factor: 15.419

4.  Coordination of Lewis acid to eta(2)-enonepalladium(0) leading to continuous structure variation from eta(2)-olefin type to eta(3)-allyl type.

Authors:  S Ogoshi; T Yoshida; T Nishida; M Morita; H Kurosawa
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

Review 5.  Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition.

Authors:  B L Feringa
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

6.  DFT studies on the mechanism of allylative dearomatization catalyzed by palladium.

Authors:  Alireza Ariafard; Zhenyang Lin
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

7.  Highly enantioselective hydrosilylation of aromatic alkenes.

Authors:  Jakob F Jensen; Bo Y Svendsen; Thomas V la Cour; Henriette L Pedersen; Mogens Johannsen
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

8.  Intramolecular coupling of allyl carboxylates with allyl stannanes and allyl silanes: a new type of reductive elimination reaction?

Authors:  María Méndez; Juan M Cuerva; Enrique Gómez-Bengoa; Diego J Cárdenas; Antonio M Echavarren
Journal:  Chemistry       Date:  2002-08-16       Impact factor: 5.236

9.  Asymmetric conjugate addition reactions of allyl- and crotylstannanes.

Authors:  David R Williams; Richard J Mullins; Nathan A Miller
Journal:  Chem Commun (Camb)       Date:  2003-09-07       Impact factor: 6.222

10.  Nickel-catalyzed 1,4-addition of trialkylboranes to alpha,beta-unsaturated esters: dramatic enhancement by addition of methanol.

Authors:  Koji Hirano; Hideki Yorimitsu; Koichiro Oshima
Journal:  Org Lett       Date:  2007-03-16       Impact factor: 6.005
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  20 in total

1.  Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Authors:  Xiben Li; Fanke Meng; Sebastian Torker; Ying Shi; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-20       Impact factor: 15.336

2.  Catalytic enantioselective conjugate allylation of unsaturated methylidene ketones.

Authors:  Laura A Brozek; Joshua D Sieber; James P Morken
Journal:  Org Lett       Date:  2011-02-02       Impact factor: 6.005

3.  Catalytic Enantioselective Addition of an Allyl Group to Ketones Containing a Tri-, a Di-, or a Monohalomethyl Moiety. Stereochemical Control Based on Distinctive Electronic and Steric Attributes of C-Cl, C-Br, and C-F Bonds.

Authors:  Diana C Fager; KyungA Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2019-09-25       Impact factor: 15.419

4.  Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.

Authors:  Ruja Shrestha; Stephanie C M Dorn; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2013-01-08       Impact factor: 15.419

5.  Pd-catalyzed enantioselective allyl-allyl cross-coupling.

Authors:  Ping Zhang; Laura A Brozek; James P Morken
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

6.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

7.  Pd-catalyzed carbonylative conjugate addition of dialkylzinc reagents to unsaturated carbonyls.

Authors:  Daniel W Custar; Hai Le; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

8.  Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones.

Authors:  Michael Z Liang; Simon J Meek
Journal:  J Am Chem Soc       Date:  2020-05-18       Impact factor: 15.419

9.  Racemic Vinylallenes in Catalytic Enantioselective Multicomponent Processes: Rapid Generation of Complexity through 1,6-Conjugate Additions.

Authors:  Youming Huang; Sebastian Torker; Xinghan Li; Juan Del Pozo; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-06       Impact factor: 15.336

10.  A boron-based synthesis of the natural product (+)-trans-dihydrolycoricidine.

Authors:  Sarah L Poe; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-31       Impact factor: 15.336
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