[3,3]-rearrangements of phosphonium ylides.
Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields. This new reaction manifold for phosphorus ylides is tolerant of a range of substitution patterns on the reactants and provides access to structurally complex intermediates for the synthesis of enzyme inhibitors, aminophosphonic acids, and natural products.
Ferguson
Marcelle L
ML
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Senecal
Todd D
TD
Groendyke
Todd M
TM
Mapp
Anna K
AK
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000438:Alcohols; D000475:Alkenes; D009943:Organophosphorus Compounds