1039458-46-2Relevant academic research and scientific papers
Selective one-pot synthesis of functionalized cyclopentenones
Varea, Teresa,Alcalde, Ana,Lopez De Dicastillo, Carolina,Ramirez De Arellano, Carmen,Cossio, Fernando P.,Asensio, Gregorio
, p. 6327 - 6331 (2012)
Double addition (1,2-1,4) of vinyl magnesium bromide to squaric acid derivatives allows the preparation of polyoxygenated cyclopentenones (8) in a one-pot procedure. The reaction occurs through the intermediate formation of octatetraenes (6). Protonation of this latter intermediate at -78 °C with TFE occurs selectively at the vinyl CH2 closer to the metallic centers. DFT studies of the cyclization step justify the observed diastereoselectivity.
