Direct Catalytic Asymmetric Addition of α-Fluoronitriles to Aldehydes

Pandur Venkatesan Balaji, Zhao Li, Akira Saito, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A fluorine-containing tetrasubstituted stereogenic center is a highly valued structural feature in medicinal chemistry. Herein, we describe the direct coupling of racemic α-fluoronitriles and aldehydes promoted by a chiral CuI/Barton's base catalytic system, delivering α-tetrasubstituted α-fluoro-β-hydroxynitriles with satisfactory stereoselection. The stereochemical course was positively biased by the combined use of asymmetrical achiral thiourea as a supplementary ligand for CuI, which significantly enhanced the stereoselectivity. Both aromatic and aliphatic aldehydes were implemented to provide densely and stereoselectively functionalized chiral building blocks with aliphatic and aromatic tails.

Original languageEnglish
Pages (from-to)15524-15527
Number of pages4
JournalChemistry - A European Journal
Volume26
Issue number67
DOIs
Publication statusPublished - 2020 Dec 1
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cooperative catalysis
  • fluorine
  • nitrile
  • thiourea

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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