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

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 proces...

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Veröffentlicht in:	Organic & biomolecular chemistry 2015-03, Vol.13 (10), p.2895-2900
Hauptverfasser:	Campbell, Craig D, Joannesse, Caroline, Morrill, Louis C, Philp, Douglas, Smith, Andrew D
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Aminopyridine - analogs & derivatives 4-Aminopyridine - chemistry 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemistry Carbon - chemistry Carbonates - chemistry Catalysis Furans - chemistry Kinetics Lewis Bases Magnetic Resonance Spectroscopy Molecular Structure Oxygen - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	1477-0520 1477-0539
DOI:	10.1039/c4ob02629b