219547-24-7Relevant academic research and scientific papers
Stereoselective phenyl migration from silicon to carbon
Studer, Armido,Bossart, Martin,Steen, Hanno
, p. 8829 - 8832 (1998)
In the present letter, the first stereoselective radical 1,5 phenyl transfer from silicon to carbon is reported. Diphenyl(trimethylsilyl)silyl ethers, the corresponding germylated and stannylated derivatives, and also some silyl ethers derived from commercially available silicon protecting groups were tested in this ipso substitution reaction. Diastereoselectivities of up to 11:1 were obtained.
Stereoselective radical aryl migration from silicon to carbon
Amrein, Stephan,Bossart, Martin,Vasella, Tomaso,Studer, Armido
, p. 4281 - 4288 (2007/10/03)
Highly diastereoselective radical 1,5 phenyl migration reactions from silicon in diarylsilyl ethers to various C-centered radicals to form the corresponding 3-phenylated alcohols are described. Functionalized aryl groups can also be transferred. The effect of the variation of the attacking radical on the aryl transfer reaction is discussed. Best results are obtained for the phenyl migration to nucleophilic secondary alkyl radicals, where high yields (up to 81%) and high selectivities (up to 95% ds) have been obtained. The mechanism of the process is discussed and a model to explain the stereochemical outcome of the reaction is presented. Finally, stereoselective 1,4 aryl migration reactions from Si to C, including a new method for the α- arylation of esters, are presented.
