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

研究成果: Article査読

22 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)2644-2648
ページ数5
ジャーナルAngewandte Chemie - International Edition
58
9
DOI
出版ステータスPublished - 2019 2月 25
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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