Readily accessible, modular, and tuneable BINOL 3,3'-perfluoroalkylsulfones: Highly efficient catalysts for enantioselective in-mediated imine allylation

Robert Kargbo, Yoko Takahashi, Santosh Bhor, Gregory R. Cook*, Guy C. Lloyd-Jones, Ian R. Shepperson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Thia-Fries rearrangement of BINOL perfluoroalkylsulfonates affords readily derivatized novel mono- and disulfone ligands in just two steps from enantiomerically pure BINOL. These electron-demanding BINOLs have been successfully applied as catalysts for indium-mediated allylation of N-acylhydrazones. A general and highly enantioselective catalytic process is described, in which the presence of two perfluoroalkylsulfone (SO2RF) groups is shown to be crucial for activity and selectivity. The allylation process affords the corresponding homoallylic amines up to 99% yield and 99% ee.

Original languageEnglish
Pages (from-to)3846-+
Number of pages3
JournalJournal of the American Chemical Society
Volume129
Issue number13
DOIs
Publication statusPublished - 4 Apr 2007

Keywords

  • GLYOXYLIC OXIME ETHER
  • ALPHA-AMINO-ACIDS
  • NEUTRAL-COORDINATE-ORGANOCATALYSTS
  • PI-ALLYLPALLADIUM COMPLEX
  • THIA-FRIES REARRANGEMENT
  • BARBIER-TYPE ALLYLATION
  • AQUEOUS-MEDIA
  • ASYMMETRIC ALLYLATION
  • ORGANOMETALLIC REACTIONS
  • HOMOALLYLIC AMINES

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