Anhydrides as α,β-unsaturated acyl ammonium precursors: isothiourea-promoted catalytic asymmetric annulation processes

Emily R. T. Robinson, Charlene Fallan, Carmen Simal, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

100 Citations (Scopus)
73 Downloads (Pure)

Abstract

The asymmetric annulation of a range of alpha,beta-unsaturated acyl ammonium intermediates, formed from isothiourea HBTM 2.1 and anhydrides with either 1,3-dicarbonyls, beta-ketoesters or azaaryl ketones gives either functionalised esters (upon ring opening), dihydropyranones or dihydropyridones in good yields (up to 93%) and high enantioselectivity (up to 97% ee).

Original languageEnglish
Pages (from-to)2193-2200
Number of pages8
JournalChemical Science
Volume4
Early online date1 Mar 2013
DOIs
Publication statusPublished - 2013

Keywords

  • Bicyclic-beta-lactones
  • Secondary benzylic alcohols
  • Dynamic kinetic resolution
  • N-heterocyclic carbenes
  • Silyl ketene acetals
  • Lewis-base catalysis
  • Enantioselective synthesis

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