Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates
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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
Campbell , C D , Joannesse , C , Morrill , L C , Philpa , D & Smith , A D 2015 , ' Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates ' Organic & Biomolecular Chemistry , vol 13 , no. 10 , pp. 2895-2900 . DOI: 10.1039/C4OB02629B
Organic & Biomolecular Chemistry
Copyright 2015 the Authors. This open access article is licensed under a Creative Commons Attribution 3.0 Unported Licence (http://creativecommons.org/licenses/by/3.0/).
The authors would like to thank the Royal Society for a University Research Fellowship (ADS), The Carnegie Trust for the Universities of Scotland (CDC and LCM) and the EPSRC (CJ) for funding, and the EPSRC National Mass Spectrometry Service Centre (Swansea).
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