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Issue 1, 2017
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Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

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Abstract

A sequence of regio- and stereoselective carbometalation followed by oxidation of ynamides leads to stereodefined fully substituted enolates that subsequently react with various functionalized allyl bromide reagents to provide the expected products possessing an enantiomerically pure quaternary carbon stereocentre in the α-position to the carbonyl group in excellent yields and enantiomeric ratios after cleavage of the oxazolidinone moiety. Three new bonds are formed in a single-pot operation.

Graphical abstract: Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

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Publication details

The article was received on 10 Jul 2016, accepted on 25 Aug 2016 and first published on 15 Sep 2016


Article type: Edge Article
DOI: 10.1039/C6SC03036J
Citation: Chem. Sci., 2017,8, 627-630
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    Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres

    Z. Nairoukh, G. G. K. S. N. Kumar, Y. Minko and I. Marek, Chem. Sci., 2017, 8, 627
    DOI: 10.1039/C6SC03036J

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