First organophosphorus radical-mediated cyclisations to afford medium-sized rings: eight-membered lactones and seven- and eight-membered lactams

S Lang, Michael James Corr, N Muir, T A Khan, F Schonebeck, J A Murphy, A H Payne, A C Williams

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

The phosphorus based radical precursors N-ethylpiperidine hypophosphite (EPHP) and diethylphosphine oxide (DEPO) are efficient reagents for carrying out the formation of seven- and eight-membered rings. Esters and amides were successfully converted into the corresponding eight-membered lactones and seven- and eight-membered lactams in good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4027-4030
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number23
DOIs
Publication statusPublished - 6 Jun 2005

Keywords

  • radical
  • phosphorus
  • DEPO
  • EPHP
  • cyclisation
  • KETYL-OLEFIN CYCLIZATION
  • CARBON BOND FORMATION
  • (ALKOXYCARBONYL)METHYL RADICALS
  • STEREOSELECTIVE-SYNTHESIS
  • 8-ENDO CYCLIZATION
  • EFFICIENT ROUTE
  • AQUEOUS-MEDIA
  • HYPOPHOSPHITE
  • WATER
  • ESTERS

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