A New Method for the Synthesis of Unsymmetrical Bis-Aldols by the Samarium(II) Iodide-Mediated Aldol Reaction of Aldehydes with Aryl or Alkyl Oxiranyl Ketones

Abstract

Abstract Unsymmetrical alkyl or aryl 2-hydroxy-1-(1-hydroxyalkyl)alkyl ketones (bis-aldols) were synthesized by the samarium(II) iodide-mediated aldol reaction of aldehydes with alkyl or aryl oxiranyl ketones. Bis-aldols were formed via the aldol reaction of aldehydes with samarium enolates generated by epoxy-fragmentation of oxiranyl ketones using two moles of samarium(II) iodide.