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

Craig Donald Campbell, Caroline Joannesse, Louis Christian Morrill, Douglas Philpa, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

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
Original languageEnglish
Pages (from-to)2895-2900
JournalOrganic & Biomolecular Chemistry
Volume13
Issue number10
Early online date3 Feb 2015
DOIs
Publication statusPublished - 14 Mar 2015

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