Organic & Biomolecular Chemistry 2008-04-21

Urea derivatives are highly active catalysts for the base-mediated generation of terminal epoxides from aldehydes and trimethylsulfonium iodide.

Sarah A Kavanagh, Alessandro Piccinini, Eimear M Fleming, Stephen J Connon

Index: Org. Biomol. Chem. 6(8) , 1339-43, (2008)

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Abstract

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.