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Issue 10, 2015
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Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

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Abstract

Triazolinylidenes promote γ-selective C-carboxylation (up to 99 : 1 regioselectivity) in the O- to C-carboxyl transfer of furanyl carbonates in contrast to DMAP that promotes preferential α-C-carboxylation with moderate regiocontrol (typically 60 : 40 regioselectivity). The generality of this process is described and a simple mechanistic and kinetic model postulated to account for the observed regioselectivity

Graphical abstract: Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

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Publication details

The article was received on 19 Dec 2014, accepted on 16 Jan 2015 and first published on 03 Feb 2015


Article type: Communication
DOI: 10.1039/C4OB02629B
Citation: Org. Biomol. Chem., 2015,13, 2895-2900
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    Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates

    C. D. Campbell, C. Joannesse, L. C. Morrill, D. Philp and A. D. Smith, Org. Biomol. Chem., 2015, 13, 2895
    DOI: 10.1039/C4OB02629B

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