Anti-Markovnikov stereoselective addition of bis(trimethylsilyl)octadiene to ketal obtained by unprecedented retro-Claisen condensation of 3-hydroxy-2,4-pentanedione bis-ketal

摘要

In the course of the Lewis acid-mediated cycloaddition of 1,8-bis(trimethylsilyl)-2,6-octadiene to bis-ketals, we have observed an unprecedented retro-Claisen condensation from the ketalisation of a 3-hydroxy-2,4-pentadione giving rise to a substituted 2,2,3-trimethoxybutane and an anti-Markovnikov stereoselective cycloaddition of the 1,8-bis(trimethylsily1)-2,6-octadiene to this latter ketal. (C) 2014 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.