Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization
A diastereoselective method for addition of a vinyl group to alpha-hydroxy hydrazones under neutral tin-free radical cyclization conditions, leading to substituted vinylglycinols, is presented. Tandem thiyl radical addition/cyclization upon a silicon-tethered vinyl group followed by treatment with potassium fluoride accomplishes a one-pot neutral vinyl addition process to afford acyclic allylic anti-hydrazino alcohols in good yield.
Friestad
GK
Department of Chemistry, University of Vermont, Burlington, Vermont 05405, USA.
Massari
SE