Literature DB >> 23780881

Enantioselective synthesis of quaternary carbon stereogenic centers through copper-catalyzed conjugate additions of aryl- and alkylaluminum reagents to acyclic trisubstituted enones.

Jennifer A Dabrowski1, Matthew T Villaume, Amir H Hoveyda.   

Abstract

Entities:  

Keywords:  N-heterocyclic carbenes; copper; enantioselective conjugate additions; organoaluminums; quaternary carbons

Mesh:

Substances:

Year:  2013        PMID: 23780881      PMCID: PMC3787522          DOI: 10.1002/anie.201304035

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


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  35 in total

1.  Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: construction of stereogenic quaternary centers.

Authors:  Magali d'Augustin; Laëticia Palais; Alexandre Alexakis
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-18       Impact factor: 15.336

2.  All-carbon quaternary stereogenic centers by enantioselective cu-catalyzed conjugate additions promoted by a chiral N-heterocyclic carbene.

Authors:  M Kevin Brown; Tricia L May; Carl A Baxter; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

3.  Dinuclear {(salen)Al} complexes display expanded scope in the conjugate cyanation of alpha,beta-unsaturated imides.

Authors:  Clément Mazet; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Recent advances in enantioselective copper-catalyzed 1,4-addition.

Authors:  Thomas Jerphagnon; M Gabriella Pizzuti; Adriaan J Minnaard; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2009-02-11       Impact factor: 54.564

5.  A practical method for enantioselective synthesis of all-carbon quaternary stereogenic centers through NHC-Cu-catalyzed conjugate additions of alkyl- and arylzinc reagents to beta-substituted cyclic enones.

Authors:  Kang-sang Lee; M Kevin Brown; Alexander W Hird; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

6.  Effect of high pressure on the organocatalytic asymmetric Michael reaction: highly enantioselective synthesis of γ-nitroketones with quaternary stereogenic centers.

Authors:  Piotr Kwiatkowski; Krzysztof Dudziński; Dawid Łyżwa
Journal:  Org Lett       Date:  2011-06-14       Impact factor: 6.005

7.  Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers.

Authors:  David Martin; Stefan Kehrli; Magali d'Augustin; Hervé Clavier; Marc Mauduit; Alexandre Alexakis
Journal:  J Am Chem Soc       Date:  2006-07-05       Impact factor: 15.419

8.  Formation of quaternary chiral centers by N-heterocyclic carbene-Cu-catalyzed asymmetric conjugate addition reactions with Grignard reagents on trisubstituted cyclic enones.

Authors:  Stefan Kehrli; David Martin; Diane Rix; Marc Mauduit; Alexandre Alexakis
Journal:  Chemistry       Date:  2010-08-23       Impact factor: 5.236

9.  Formation of vinyl-, vinylhalide- or acyl-substituted quaternary carbon stereogenic centers through NHC-Cu-catalyzed enantioselective conjugate additions of Si-containing vinylaluminums to β-substituted cyclic enones.

Authors:  Tricia L May; Jennifer A Dabrowski; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-12-20       Impact factor: 15.419

10.  Asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc reagents to 2-aryl acetate derivatives.

Authors:  Ashraf Wilsily; Eric Fillion
Journal:  Org Lett       Date:  2008-05-30       Impact factor: 6.005

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  12 in total

1.  Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates.

Authors:  Pavel Starkov; Jared T Moore; Douglas C Duquette; Brian M Stoltz; Ilan Marek
Journal:  J Am Chem Soc       Date:  2017-07-07       Impact factor: 15.419

2.  Acyclic Quaternary Carbon Stereocenters via Enantioselective Transition Metal Catalysis.

Authors:  Jiajie Feng; Michael Holmes; Michael J Krische
Journal:  Chem Rev       Date:  2017-09-14       Impact factor: 60.622

3.  Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters.

Authors:  Chun Zhang; Celine B Santiago; Jennifer M Crawford; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-12-10       Impact factor: 15.419

4.  Enantioselective Palladium-Catalyzed Alkenylation of Trisubstituted Alkenols To Form Allylic Quaternary Centers.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-10-25       Impact factor: 15.419

5.  Synthesis of Secondary and Tertiary Alkylboranes via Formal Hydroboration of Terminal and 1,1-Disubstituted Alkenes.

Authors:  Hilary A Kerchner; John Montgomery
Journal:  Org Lett       Date:  2016-10-27       Impact factor: 6.005

6.  Catalytic diastereo- and enantioselective additions of versatile allyl groups to N-H ketimines.

Authors:  Hwanjong Jang; Filippo Romiti; Sebastian Torker; Amir H Hoveyda
Journal:  Nat Chem       Date:  2017-07-17       Impact factor: 24.427

7.  Enantioselective construction of remote quaternary stereocentres.

Authors:  Tian-Sheng Mei; Harshkumar H Patel; Matthew S Sigman
Journal:  Nature       Date:  2014-04-09       Impact factor: 49.962

8.  Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones.

Authors:  Zhenbo Gao; Stephen P Fletcher
Journal:  Chem Sci       Date:  2016-09-02       Impact factor: 9.825

9.  Copper-catalyzed arylation of alkyl halides with arylaluminum reagents.

Authors:  Bijay Shrestha; Ramesh Giri
Journal:  Beilstein J Org Chem       Date:  2015-12-02       Impact factor: 2.883

10.  Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.

Authors:  Qi Zhou; Kelsey M Cobb; Tianyu Tan; Mary P Watson
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419

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