Selective %26quot;One-Pot%26quot; Synthesis of Functionalized Cyclopentenones

作者:Varea Teresa*; Alcalde Ana; Lopez de Dicastillo Carolina; Ramirez de Arellano Carmen; Cossio Fernando P; Asensio Gregorio
来源:Journal of Organic Chemistry, 2012, 77(14): 6327-6331.
DOI:10.1021/jo300806y

摘要

Double addition (1,2-1,4) of vinyl magnesium bromide to squaric acid derivatives allows the preparation of polyoxygenated cyclopentenones (8) in a %26quot;one-pot%26quot; procedure. The reaction occurs through the intermediate formation of octatetraenes (6). Protonation of this latter intermediate at -78 degrees C with TFE occurs selectively at the vinyl CH2 closer to the metallic centers. DFT studies of the cyclization step justify the observed distereoselectivity.

  • 出版日期2012-7-20