Achiral Trisubstituted Thioureas as Secondary Ligands to Cu I Catalysts: Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Imines

Pandur Venkatesan Balaji, Lennart Brewitz, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Thioureas have emerged as effective hydrogen-bonding catalysts over the last two decades, and they are broadly utilized in asymmetric catalysis. We report that achiral trisubstituted thioureas function as beneficial secondary ligands to Cu I catalysts, thereby enabling highly diastereo- and enantioselective addition of α-fluoronitriles to imines. The structure of the thiourea significantly affects the reaction outcome, and kinetic experiments indicate that the thioureas enhance the stereocontrol by binding to the Cu I complex. The reaction products can be readily transformed into valuable β-amino acid derivatives bearing a fluorinated tetrasubstituted stereogenic center.

Original languageEnglish
Pages (from-to)2644-2648
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number9
DOIs
Publication statusPublished - 2019 Feb 25
Externally publishedYes

Keywords

  • asymmetric catalysis
  • atom economy
  • copper
  • nitriles
  • thiourea

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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