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Issue 1, 2017
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Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones

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Abstract

Synthetic methods for the selective formation of all carbon quaternary centres in non-cyclic systems are rare. Here we report highly enantioselective Cu-catalytic asymmetric conjugate addition of alkylzirconium species to twelve different acyclic trisubstituted enones. A variety of sp3-hybridized nucleophiles generated by in situ hydrozirconation of alkenes with the Schwartz reagent can be introduced, giving linear products bearing quaternary centres with up to 98% ee. The method is tolerant of several important functional groups and 27 total examples are reported. The method uses a new chiral nonracemic phosphoramidite ligand in a complex with copper triflate as the catalyst. This work allows the straightforward stereocontrolled formation of a valuable structural motif using only a catalytic amount of chiral reagent.

Graphical abstract: Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones

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Publication details

The article was received on 24 Jun 2016, accepted on 01 Sep 2016 and first published on 02 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC02811J
Citation: Chem. Sci., 2017,8, 641-646
  • Open access: Creative Commons BY-NC license
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    Acyclic quaternary centers from asymmetric conjugate addition of alkylzirconium reagents to linear trisubstituted enones

    Z. Gao and S. P. Fletcher, Chem. Sci., 2017, 8, 641
    DOI: 10.1039/C6SC02811J

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