631902-73-3Relevant academic research and scientific papers
Tandem thiyl radical addition and cyclization of chiral hydrazones using a silicon-tethered alkyne
Friestad, Gregory K.,Jiang, Tao,Fioroni, Gina M.
, p. 2853 - 2856 (2003)
A diastereoselective method for addition of a trans-2-(phenylthio)vinyl group to α-hydroxy hydrazones is presented. An ethynyl group, tethered to α-hydroxy hydrazones via a silicon tether, undergoes thiyl radical addition and cyclization under neutral tin-free conditions. In the same pot, desilylation with potassium fluoride or tetrabutylammonium fluoride affords (E)-vinylsulfides. The one-pot process is the synthetic equivalent of an acetaldehyde Mannich reaction with acyclic stereocontrol.
