Isothiourea-catalyzed asymmetric synthesis of β-lactams and β-amino esters from arylacetic acid derivatives and N-sulfonylaldimines

Siobhan R. Smith, James Douglas, Hugues Prevet, Peter Shapland, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

Abstract

The isothiourea HBTM-2.1 (5 mol %) catalyzes the asymmetric formal [2 + 2] cycloaddition of both arylacetic acids (following activation with tosyl chloride) and preformed 2-arylacetic anhydrides with N-sulfonylaldimines, generating stereodefined 2,3-diaryl-β-amino esters (after ring-opening) and 3,4-diaryl-anti-β-lactams, respectively, with high diastereocontrol (up to >95:5 dr) and good to excellent enantiocontrol. Deprotection of the N-tosyl substituent within the β-lactam framework was possible without racemization by treatment with SmI2.

Original languageEnglish
Pages (from-to)1626-1639
Number of pages14
JournalThe Journal of Organic Chemistry
Volume79
Issue number4
Early online date5 Feb 2014
DOIs
Publication statusPublished - 21 Feb 2014

Keywords

  • Human Cytomegalovirus Protease
  • Promoted Bis-Cyclizations
  • Acyl Transfer Catalyst
  • Pure Lithium Amides
  • Enantioselective Synthesis
  • Kinugasa Reaction
  • Aldol-Lactonization
  • Staudinger Reaction
  • Kinetic Resolution
  • Dyotropic Rearrangements

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