An isothiourea-catalyzed asymmetric [2,3]-rearrangement of allylic ammonium ylides

Thomas H. West, David S. B. Daniels, Alexandra M. Z. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

125 Citations (Scopus)
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Abstract

Benzotetramisole promotes the catalytic asymmetric [2,,3]-rearrangement of allylic quaternary ammonium salts (either isolated or prepared in situ from p-nitrophenyl bromoacetate and the corresponding allylic amine), generating syn-alpha-amino acid derivatives with excellent diastereo- and enantioselectivity (up to >95:5 dr; up to >99% ee).

Original languageEnglish
Pages (from-to)4476-4479
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number12
Early online date3 Mar 2014
DOIs
Publication statusPublished - 26 Mar 2014

Keywords

  • Ketene-Forming Eliminations
  • Amino-Acid Derivatives
  • Acyl Transfer Catalyst
  • One-Pot Synthesis
  • Kinetic Resolution
  • Organocatalytic Activation
  • Aryl Phenylacetates
  • Rearrangement
  • Esters
  • Benzotetramisole

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