1160587-06-3Relevant academic research and scientific papers
Irreversible endo-Selective Diels-Alder Reactions of Substituted Alkoxyfurans: A General Synthesis of endo-Cantharimides
Foster, Robert W.,Benhamou, Laure,Porter, Michael J.,Bu?ar, Dejan-Kre?imir,Hailes, Helen C.,Tame, Christopher J.,Sheppard, Tom D.
supporting information, p. 6107 - 6114 (2015/04/14)
The [4+2] cycloaddition of 3-alkoxyfurans with N-substituted maleimides provides the first general route for preparing endo-cantharimides. Unlike the corresponding reaction with 3H furans, the reaction can tolerate a broad range of 2-substitued furans including alkyl, aromatic, and heteroaromatic groups. The cycloaddition products were converted into a range of cantharimide products with promising lead-like properties for medicinal chemistry programs. Furthermore, the electron-rich furans are shown to react with a variety of alternative dienophiles to generate 7-oxabicyclo[2.2.1]heptane derivatives under mild conditions. DFT calculations have been performed to rationalize the activation effect of the 3-alkoxy group on a furan Diels-Alder reaction.
Gold catalysed synthesis of 3-alkoxyfurans at room temperature
Pennell, Matthew N.,Foster, Robert W.,Turner, Peter G.,Hailes, Helen C.,Tame, Christopher J.,Sheppard, Tom D.
supporting information, p. 1302 - 1304 (2014/01/23)
Synthetically important 3-alkoxyfurans can be prepared efficiently via treatment of acetal-containing propargylic alcohols (obtained from the addition of 3,3-diethoxypropyne to aldehydes) with 2 mol% gold catalyst in an alcohol solvent at room temperature. The resulting furans show useful reactivity in a variety of subsequent transformations. The Royal Society of Chemistry.
Flexible synthesis of pyrimidines with chiral monofluorinated and difluoromethyl side chains
Bannwarth, Pierre,Valleix, Alain,Gree, Danielle,Gree, Rene
experimental part, p. 4646 - 4649 (2009/09/25)
(Chemical Equation Presented) Chiral pyrimidines with a fluorine atom in the benzylic position are easily accessible in high enantiomeric excesses from optically active propargylic intermediates by two complementary routes. Both the use of optically activ
