Diastereoselective free radical halogenation, azidation, and rearrangement of beta-silyl Barton esters.
[reaction: see text] Barton esters of beta-silylcarboxylic acids were decomposed by photolysis alone in organic solvents or in the presence of ethanesulfonyl azide or bromotrichloromethane. Products of the reaction, beta-silylthiopyridyl ethers, beta-silyl azides, or alkenes, were formed with significant control of stereochemistry.
Masterson
Douglas S
DS
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA.
Porter
Ned A
NA
D001386:Azides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010782:Photolysis; D013237:Stereoisomerism
D001386:Azides; D004952:Esters; D005609:Free Radicals; D006219:Halogens