Literature DB >> 25634651

Enantioselective copper(I)-phosphoramidite catalyzed addition of alkylzirconium species to acyclic enones.

Philippe M C Roth1, Stephen P Fletcher.   

Abstract

Catalytic asymmetric conjugate addition reactions of alkylzirconium species to acyclic enones are reported. The alkylzirconium nucleophiles are generated in situ by hydrozirconation of alkenes with the Schwartz reagent. The reaction proceeds under mild and convenient conditions. A variety of functionalized nucleophiles can be used, and the method tolerates some variation in enone scope. The method uses a new chiral nonracemic phosphoramidite ligand in a complex with copper triflate.

Entities:  

Year:  2015        PMID: 25634651     DOI: 10.1021/acs.orglett.5b00021

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  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

2.  Catalytic Enantioselective Addition of Organozirconium Reagents to Aldehydes.

Authors:  Ricard Solà; Marcos Veguillas; María José González-Soria; Nicholas Carter; M Angeles Fernández-Ibáñez; Beatriz Maciá
Journal:  Molecules       Date:  2018-04-20       Impact factor: 4.411

3.  Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans.

Authors:  Emeline Rideau; Stephen P Fletcher
Journal:  Beilstein J Org Chem       Date:  2015-12-03       Impact factor: 2.883

4.  Retooling Asymmetric Conjugate Additions for Sterically Demanding Substrates with an Iterative Data-Driven Approach.

Authors:  Alexandre V Brethomé; Robert S Paton; Stephen P Fletcher
Journal:  ACS Catal       Date:  2019-07-02       Impact factor: 13.084

  4 in total

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