58683-58-2Relevant articles and documents
New chiral synthons for efficient introduction of bispropionates via stereospecific oxonia-cope rearrangements
Chen, Yi-Hung,McDonald, Frank E.
, p. 4568 - 4569 (2007/10/03)
Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including α-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal. Copyright
