Urea derivatives are highly active catalysts for the base-mediated generation of terminal epoxides from aldehydes and trimethylsulfonium iodide.
N,N'-Diarylureas have been shown to efficiently catalyse sulfonium ylide-mediated aldehyde epoxidation reactions for the first time. These processes are of broad scope and can be coupled with a subsequent Cu(II) ion-catalysed Meinwald rearrangement to give an efficient and convenient protocol for aldehyde homologation without intermediate purification.
Kavanagh
Sarah A
SA
Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.
Piccinini
Alessandro
A
Fleming
Eimear M
EM
Connon
Stephen J
SJ
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012972:Sodium Hydroxide / Q000737:chemistry; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry*
D000447:Aldehydes; D004852:Epoxy Compounds; D013452:Sulfonium Compounds; D012972:Sodium Hydroxide; C009581:trimethylsulfonium; D014508:Urea