163034-48-8Relevant academic research and scientific papers
Chemoselective Carbonyl Allylations with Alkoxyallylsiletanes
Spaltenstein, Paul,Cummins, Elizabeth J.,Yokuda, Kelly-Marie,Kowalczyk, Tim,Clark, Timothy B.,O'Neil, Gregory W.
, p. 4421 - 4428 (2019)
Alkoxyallylsiletanes are capable of highly chemo- and diastereoselective carbonyl allylsilylations. Reactive substrates include salicylaldehydes and glyoxylic acids. Chemoselectivity in these reactions is thought to arise from a mechanism involving first exchange of the alkyoxy group on silicon with a substrate hydroxyl followed by activation of a nearby carbonyl by the Lewis acidic siletane and intramolecular allylation. In this way, substrates containing multiple reactive carbonyl groups (e.g., dialdehyde or triketone) can be selectively monoallylated, even overcoming inherent electrophilicity bias.
Iodine-mediated rearrangements of diallylsilanes
O'Neil, Gregory W.,Cummins, Elizabeth J.
, p. 3406 - 3409 (2017)
Diallylsilanes can be made to rearrange upon treatment with I2. Of the silanes tested, diallyldiphenylsilane showed the greatest propensity to undergo this intramolecular carbocation allylation process. After etherification of the initially for
