Direct Catalytic Asymmetric Addition of Acetonitrile to Aldimines

Akira Saito, Naoya Kumagai, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Despite significant advances in catalytic asymmetric reactions with decent stereocontrol, those using acetonitrile as a pronucleophile are often disregarded due to their low reactivity and insufficient enantioselectivity. Herein we report the resurgence of this reaction in the chemical toolbox with high enantioselectivity (avg. > 95% ee). The combined use of a Ni(II) complex ligated with a chiral biscarbene and tBuOK engages acetonitrile in the catalytic generation of an α-cyanocarbanion and subsequent highly enantioselective addition to aldimines.

Original languageEnglish
Pages (from-to)8187-8190
Number of pages4
JournalOrganic Letters
Volume21
Issue number20
DOIs
Publication statusPublished - 2019 Oct 18
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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