Direct Catalytic Asymmetric Addition of Alkylnitriles to Aldehydes with Designed Nickel–Carbene Complexes

Akira Saito, Shinya Adachi, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

Abstract

A direct catalytic asymmetric addition of acetonitrile to aldehydes that realizes over 90 % ee is the ultimate challenge in alkylnitrile addition chemistry. Herein, we report achieving high enantioselectivity by the strategic use of a sterically demanding NiII pincer carbene complex, which afforded highly enantioenriched β-hydroxynitriles. This highly atom-economical process paves the way for exploiting inexpensive acetonitrile as a promising C2 building block in a practical synthetic toolbox for asymmetric catalysis.

Original languageEnglish
Pages (from-to)8739-8743
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number16
DOIs
Publication statusPublished - 2021 Apr 12
Externally publishedYes

Keywords

  • aldehydes
  • enantioselectivity
  • homogeneous catalysis
  • nickel
  • nitriles

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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