Stereoelectronic Effects in the Fragmentation of γ‑Silyloxy-β-hydroxy-α-diazocarbonyl Compounds
journal contributionposted on 02.11.2012 by Nitinkumar D. Jabre, Matthias Brewer
Any type of content formally published in an academic journal, usually following a peer-review process.
A series of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds were prepared as fragmentation substrates to probe the hypothesis that steric interactions between the diazo ester and adjacent silyloxy group can play an important role in determining the success of fragmentations. Proper stereoelectronic alignment of the diazo ester and the departing hydroxyl group is necessary for productive fragmentation to occur.