Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition-Lactonizations

Dorine Belmessieri, Louis Christian Morrill, Carmen Simal Fernandez, Alexandra Martha Zoya Slawin, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

230 Citations (Scopus)

Abstract

Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

Original languageEnglish
Pages (from-to)2714-2720
Number of pages7
JournalJournal of the American Chemical Society
Volume133
Issue number8
DOIs
Publication statusPublished - 2 Mar 2011

Keywords

  • DIELS-ALDER REACTIONS
  • N-HETEROCYCLIC CARBENES
  • BICYCLIC-BETA-LACTONES
  • ACYL-TRANSFER CATALYST
  • SECONDARY BENZYLIC ALCOHOLS
  • HIGHLY ENANTIOSELECTIVE SYNTHESIS
  • EFFECTIVE KINETIC RESOLUTION
  • PROMOTED BIS-CYCLIZATIONS
  • DELTA-LACTONES
  • ALPHA,BETA-UNSATURATED ALDEHYDES

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