Regiodivergent Lewis base-promoted O- to C-carboxyl transfer of furanyl carbonates
| Autor: | Douglas Philp, Craig D. Campbell, Andrew D. Smith, Louis C. Morrill, Caroline Joannesse |
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| Přispěvatelé: | University of St Andrews. School of Chemistry, University of St Andrews. Biomedical Sciences Research Complex, University of St Andrews. EaSTCHEM |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Magnetic Resonance Spectroscopy
Molecular Structure Kinetic model Chemistry Stereochemistry Organic Chemistry Carbonates NDAS Regioselectivity Stereoisomerism QD Chemistry Biochemistry Carbon Catalysis Oxygen Kinetics 4-Butyrolactone Lewis Bases QD Lewis acids and bases 4-Aminopyridine Physical and Theoretical Chemistry Furans |
| Popis: | 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). 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 Publisher PDF |
| Databáze: | OpenAIRE |
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