Stereoselective Radical Aryl Migration from Silicon to Carbon

S Amrein, M Bossart, T Vasella…

Index: Amrein, Stephan; Bossart, Martin; Vasella, Tomaso; Studer, Armido Journal of Organic Chemistry, 2000 , vol. 65, # 14 p. 4281 - 4288

Full Text: HTML

Citation Number: 37

Abstract

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 ...