Literature DB >> 23184884

Effect of multinuclear copper/aluminum complexes in highly asymmetric conjugate addition of trimethylaluminum to acyclic enones.

Kohei Endo1, Daisuke Hamada, Sayuri Yakeishi, Takanori Shibata.   

Abstract

Al and friends: asymmetric conjugate addition of Me(3)Al to β,β-disubstituted α,β-unsaturated ketones in the presence copper and L1 leads to a highly efficient construction of an all-carbon-substituted chiral quaternary center. This result is the first example of an asymmetric conjugate addition of Me(3)Al to acyclic enones to give a chiral quaternary carbon center with excellent yield and enantioselectivity under mild reaction conditions.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2012        PMID: 23184884     DOI: 10.1002/anie.201206297

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


  6 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

Review 2.  Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress.

Authors:  Zhigeng Lin; Baoying Huang; Lufeng Ouyang; Liyao Zheng
Journal:  Molecules       Date:  2022-06-02       Impact factor: 4.927

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

Authors:  Jennifer A Dabrowski; Matthew T Villaume; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-18       Impact factor: 15.336

4.  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

5.  Enantioselective conjugate hydrosilylation of α,β-unsaturated ketones.

Authors:  Huan Yang; Guanglin Weng; Dongmei Fang; Changjiang Peng; Yuanyuan Zhang; Xiaomei Zhang; Zhouyu Wang
Journal:  RSC Adv       Date:  2019-04-12       Impact factor: 4.036

Review 6.  Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors.

Authors:  Delphine Pichon; Jennifer Morvan; Christophe Crévisy; Marc Mauduit
Journal:  Beilstein J Org Chem       Date:  2020-02-17       Impact factor: 2.883

  6 in total

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