Diastereoselective vinyl addition to chiral hydrazones via tandem thiyl radical addition and silicon-tethered cyclization

Abstract

(equation presented) A diastereoselective method for addition of a vinyl group to α-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-hyrazino alcohols in good yield.