alpha-Ketophosphonates as ester surrogates: isothiourea-catalyzed asymmetric diester and lactone synthesis

Siobhan R. Smith, Stuart M. Leckie, Reuben Holmes, James Douglas, Charlene Fallan, Peter Shapland, David Pryde, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

Isothiourea HBTM-2.1 catalyzes the asymmetric Michael addition/lactonization of aryl- and alkenylacetic acids using α-keto-β,γ-unsaturated phosphonates as α,β-unsaturated ester surrogates, giving access to a diverse range of stereodefined lactones or
enantioenriched functionalized diesters upon ring-opening.

Original languageEnglish
Pages (from-to)2506-2509
Number of pages4
JournalOrganic Letters
Volume16
Issue number9
Early online date15 Apr 2014
DOIs
Publication statusPublished - 2 May 2014

Keywords

  • Bicyclic-beta-lactones
  • Bis(oxazolinyl)pyridine-scandium(III) triflate complexes
  • Friedel-Crafts alkylations
  • Acyl transfer catalyst
  • Diels-Alder reactions
  • Aldol-Lactonization
  • Dyotropic Rearrangements
  • Keto Acids
  • Organocatalysis
  • Michael

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