Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids

Louis C. Morrill, Samuel M. Smith, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)
1 Downloads (Pure)

Abstract

Isothiourea HBTM-2.1 promotes the catalytic asymmetric alpha-functionalization of 3-alkenoic acids through formal [2 + 2] cycloadditions with N-tosyl aldimines and formal [4 + 2] cycloadditions with either 4-aryltrifluoromethyl enones or N-aryl-N-aroyl diazenes, providing useful synthetic building blocks in good yield and with excellent enantiocontrol (up to >99% ee). Stereodefined products are amenable to further synthetic elaboration through manipulation of the olefinic functionality.

Original languageEnglish
Pages (from-to)1640-1655
Number of pages16
JournalThe Journal of Organic Chemistry
Volume79
Issue number4
Early online date5 Feb 2014
DOIs
Publication statusPublished - 21 Feb 2014

Keywords

  • Bicyclic-Beta-Lactones
  • Enantioselective Gamma-Amination
  • Carbonylative 2+2 Cycloaddition
  • Catalyzed Aldol-Lactonization
  • Promoted Bis-Cyclizations
  • Acyl Transfer Catalyst
  • Delta-Lactones
  • Dyotropic Rearrangements
  • Efficient Synthesis
  • Ncal Reactions

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