Literature DB >> 26961751

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles.

Hirohisa Ohmiya1, Heng Zhang2, Saori Shibata2, Ayumi Harada2, Masaya Sawamura3.   

Abstract

Copper-catalyzed enantioselective allylic alkylation of azoles with γ,γ-disubstituted primary allylic phosphates was achieved using a new chiral N-heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all-carbon quaternary stereogenic center at the position α to the heteroaromatic ring.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic compounds; asymmetric catalysis; carbenes; copper; heterocycles

Year:  2016        PMID: 26961751     DOI: 10.1002/anie.201600619

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


  7 in total

1.  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

2.  Cyclometalated Iridium-PhanePhos Complexes Are Active Catalysts in Enantioselective Allene-Fluoral Reductive Coupling and Related Alcohol-Mediated Carbonyl Additions That Form Acyclic Quaternary Carbon Stereocenters.

Authors:  Leyah A Schwartz; Michael Holmes; Gilmar A Brito; Théo P Gonçalves; Jeffery Richardson; J Craig Ruble; Kuo-Wei Huang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-01-25       Impact factor: 15.419

Review 3.  N-Heterocyclic Carbene Complexes in C-H Activation Reactions.

Authors:  Qun Zhao; Guangrong Meng; Steven P Nolan; Michal Szostak
Journal:  Chem Rev       Date:  2020-01-22       Impact factor: 60.622

Review 4.  Enantioselective Formation of Quaternary Centers by Allylic Alkylation with First-Row Transition-Metal Catalysts.

Authors:  Lars Süsse; Brian M Stoltz
Journal:  Chem Rev       Date:  2021-02-11       Impact factor: 60.622

Review 5.  Recent Advances in Catalysis Involving Bidentate N-Heterocyclic Carbene Ligands.

Authors:  Abdollah Neshat; Piero Mastrorilli; Ali Mousavizadeh Mobarakeh
Journal:  Molecules       Date:  2021-12-24       Impact factor: 4.411

6.  Additive-Free Pd-Catalyzed α-Allylation of Imine-Containing Heterocycles.

Authors:  Marko Kljajic; Johannes G Puschnig; Hansjörg Weber; Rolf Breinbauer
Journal:  Org Lett       Date:  2016-12-12       Impact factor: 6.005

7.  Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol-carbene ligands.

Authors:  Shohei Mimura; Sho Mizushima; Yohei Shimizu; Masaya Sawamura
Journal:  Beilstein J Org Chem       Date:  2020-03-31       Impact factor: 2.883

  7 in total

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