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Issue 50, 2015
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A detachable ester bond enables perfect Z-alkylations of olefins for the synthesis of tri- and tetrasubstituted alkenes

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Abstract

2-Vinyl-substituted phenol and an alpha-bromoester undergo a tandem esterification–alkylation reaction in the presence of a Cu–amine catalyst system to produce benzene-fused lactone. Z-Alkylated styrene is obtained after hydrolysis of the lactone with perfect selectivity. The simple protocol developed in this work opens a new avenue in the multi-substitution chemistry of alkenes.

Graphical abstract: A detachable ester bond enables perfect Z-alkylations of olefins for the synthesis of tri- and tetrasubstituted alkenes

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The article was received on 27 Apr 2015, accepted on 12 May 2015 and first published on 12 May 2015


Article type: Communication
DOI: 10.1039/C5CC03474D
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Chem. Commun., 2015,51, 10154-10157

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    A detachable ester bond enables perfect Z-alkylations of olefins for the synthesis of tri- and tetrasubstituted alkenes

    T. Nishikata, K. Nakamura, Y. Inoue and S. Ishikawa, Chem. Commun., 2015, 51, 10154
    DOI: 10.1039/C5CC03474D

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